IL91004A - Regioselective synthesis of 1,3-DI-(6-O-sucrose)1,1,3,3-tetra (hydrocarbyl) distannoxane derivatives - Google Patents

Regioselective synthesis of 1,3-DI-(6-O-sucrose)1,1,3,3-tetra (hydrocarbyl) distannoxane derivatives

Info

Publication number: IL91004A
Authority: IL; Israel
Prior art keywords: sucrose; distannoxane; hydrocarbyl; reaction; tetra
Prior art date: 1988-07-18

Application number

IL9100489A

Other languages

English (en)

Other versions

IL91004A0 (en

Original Assignee

Noramco Inc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1988-07-18

Filing date

1989-07-17

Publication date

1994-04-12

1989-07-17 Application filed by Noramco Inc filed Critical Noramco Inc

1990-02-09 Publication of IL91004A0 publication Critical patent/IL91004A0/xx

1994-04-12 Publication of IL91004A publication Critical patent/IL91004A/en

Links

239000005720 sucrose Substances 0.000 title claims abstract description 76
125000001183 hydrocarbyl group Chemical group 0.000 title claims description 26
230000015572 biosynthetic process Effects 0.000 title description 9
238000003786 synthesis reaction Methods 0.000 title description 8
229930006000 Sucrose Natural products 0.000 claims abstract description 63
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 claims abstract description 61
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 87
238000006243 chemical reaction Methods 0.000 claims description 46
238000000034 method Methods 0.000 claims description 38
JGFBRKRYDCGYKD-UHFFFAOYSA-N dibutyl(oxo)tin Chemical group CCCC[Sn](=O)CCCC JGFBRKRYDCGYKD-UHFFFAOYSA-N 0.000 claims description 24
239000000203 mixture Substances 0.000 claims description 20
229910001887 tin oxide Inorganic materials 0.000 claims description 13
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 claims description 12
239000012429 reaction media Substances 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
238000011065 in-situ storage Methods 0.000 claims description 9
KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims description 8
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
FJEKUEUBQQWPBY-UHFFFAOYSA-N 1$l^{2}-stanninane Chemical compound C1CC[Sn]CC1 FJEKUEUBQQWPBY-UHFFFAOYSA-N 0.000 claims 2
AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical group CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 claims 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims 1
AIXAANGOTKPUOY-UHFFFAOYSA-N carbachol Chemical group [Cl-].C[N+](C)(C)CCOC(N)=O AIXAANGOTKPUOY-UHFFFAOYSA-N 0.000 claims 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 62
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 40
AFHCRQREQZIDSI-OVUASUNJSA-N [(2r,3s,4s,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3,4,5-trihydroxyoxan-2-yl]methyl benzoate Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](COC(=O)C=2C=CC=CC=2)O1 AFHCRQREQZIDSI-OVUASUNJSA-N 0.000 description 38
AFHCRQREQZIDSI-UHFFFAOYSA-N sucrose-6-benzoate Natural products OC1C(O)C(CO)OC1(CO)OC1C(O)C(O)C(O)C(COC(=O)C=2C=CC=CC=2)O1 AFHCRQREQZIDSI-UHFFFAOYSA-N 0.000 description 38
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
239000000243 solution Substances 0.000 description 28
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
239000000047 product Substances 0.000 description 23
229910052786 argon Inorganic materials 0.000 description 20
239000007787 solid Substances 0.000 description 20
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 19
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
238000002360 preparation method Methods 0.000 description 15
238000004128 high performance liquid chromatography Methods 0.000 description 14
150000001875 compounds Chemical class 0.000 description 13
238000010992 reflux Methods 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
239000002904 solvent Substances 0.000 description 10
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
239000000376 reactant Substances 0.000 description 9
239000006188 syrup Substances 0.000 description 9
235000020357 syrup Nutrition 0.000 description 9
-1 HYDROXYL GROUPS Chemical group 0.000 description 8
239000002253 acid Substances 0.000 description 7
239000002002 slurry Substances 0.000 description 7
150000003606 tin compounds Chemical class 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000005917 acylation reaction Methods 0.000 description 6
150000003445 sucroses Chemical class 0.000 description 6
125000002252 acyl group Chemical group 0.000 description 5
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
150000002989 phenols Chemical class 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000000463 material Substances 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
238000005481 NMR spectroscopy Methods 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
150000008064 anhydrides Chemical class 0.000 description 3
125000003710 aryl alkyl group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
239000012043 crude product Substances 0.000 description 3
125000000753 cycloalkyl group Chemical group 0.000 description 3
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical class OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
ZXDVQYBUEVYUCG-UHFFFAOYSA-N dibutyltin(2+);methanolate Chemical compound CCCC[Sn](OC)(OC)CCCC ZXDVQYBUEVYUCG-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
SYDJVRWZOWPNNO-UHFFFAOYSA-N sucrose-benzoate Natural products OCC1OC(OC2(COC(=O)c3ccccc3)OC(CO)C(O)C2O)C(O)C(O)C1O SYDJVRWZOWPNNO-UHFFFAOYSA-N 0.000 description 3
239000006228 supernatant Substances 0.000 description 3
238000010792 warming Methods 0.000 description 3
FVVCFHXLWDDRHG-UPLOTWCNSA-N (2s,3r,4s,5r,6r)-2-[(2r,3s,4r,5r,6r)-6-[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](O)[C@@H](O)[C@@H](CO)O2)O)[C@@H](CO)O1 FVVCFHXLWDDRHG-UPLOTWCNSA-N 0.000 description 2
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
239000011358 absorbing material Substances 0.000 description 2
239000008122 artificial sweetener Substances 0.000 description 2
235000021311 artificial sweeteners Nutrition 0.000 description 2
238000003556 assay Methods 0.000 description 2
238000006480 benzoylation reaction Methods 0.000 description 2
150000001720 carbohydrates Chemical class 0.000 description 2
235000014633 carbohydrates Nutrition 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
238000001816 cooling Methods 0.000 description 2
MLIREBYILWEBDM-UHFFFAOYSA-N cyanoacetic acid Chemical compound OC(=O)CC#N MLIREBYILWEBDM-UHFFFAOYSA-N 0.000 description 2
YRYKAYLGQYRCCL-UHFFFAOYSA-N dimethoxy(stannyloxy)stannane Chemical compound CO[SnH](OC)O[SnH3] YRYKAYLGQYRCCL-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
LQRUPWUPINJLMU-UHFFFAOYSA-N dioctyl(oxo)tin Chemical compound CCCCCCCC[Sn](=O)CCCCCCCC LQRUPWUPINJLMU-UHFFFAOYSA-N 0.000 description 2
NWADXBLMWHFGGU-UHFFFAOYSA-N dodecanoic anhydride Chemical compound CCCCCCCCCCCC(=O)OC(=O)CCCCCCCCCCC NWADXBLMWHFGGU-UHFFFAOYSA-N 0.000 description 2
238000010828 elution Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000000499 gel Substances 0.000 description 2
VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
229940070765 laurate Drugs 0.000 description 2
239000007788 liquid Substances 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
125000003835 nucleoside group Chemical group 0.000 description 2
LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
238000001448 refractive index detection Methods 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
230000002194 synthesizing effect Effects 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
238000001291 vacuum drying Methods 0.000 description 2
239000008096 xylene Substances 0.000 description 2
OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
229940093475 2-ethoxyethanol Drugs 0.000 description 1
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical compound OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 1
OTLNPYWUJOZPPA-UHFFFAOYSA-N 4-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1 OTLNPYWUJOZPPA-UHFFFAOYSA-N 0.000 description 1
QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229910004373 HOAc Inorganic materials 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
239000005642 Oleic acid Substances 0.000 description 1
ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
APQHKWPGGHMYKJ-UHFFFAOYSA-N Tributyltin oxide Chemical compound CCCC[Sn](CCCC)(CCCC)O[Sn](CCCC)(CCCC)CCCC APQHKWPGGHMYKJ-UHFFFAOYSA-N 0.000 description 1
239000006096 absorbing agent Substances 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000007259 addition reaction Methods 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
230000000903 blocking effect Effects 0.000 description 1
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
150000001719 carbohydrate derivatives Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-YPZZEJLDSA-N carbon-10 atom Chemical group [10C] OKTJSMMVPCPJKN-YPZZEJLDSA-N 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
PYRZPBDTPRQYKG-UHFFFAOYSA-N cyclopentene-1-carboxylic acid Chemical compound OC(=O)C1=CCCC1 PYRZPBDTPRQYKG-UHFFFAOYSA-N 0.000 description 1
238000001514 detection method Methods 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
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238000010790 dilution Methods 0.000 description 1
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230000003292 diminished effect Effects 0.000 description 1
LLAXWOADZXHVAM-UHFFFAOYSA-L diphenoxy(stannyloxy)stannane phenol Chemical compound O(C1=CC=CC=C1)[SnH](O[SnH3])OC1=CC=CC=C1.C1(=CC=CC=C1)O LLAXWOADZXHVAM-UHFFFAOYSA-L 0.000 description 1
229910000396 dipotassium phosphate Inorganic materials 0.000 description 1
150000002016 disaccharides Chemical class 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
238000003379 elimination reaction Methods 0.000 description 1
238000005886 esterification reaction Methods 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
229940052303 ethers for general anesthesia Drugs 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
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239000011521 glass Substances 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
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150000002430 hydrocarbons Chemical class 0.000 description 1
125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
239000011344 liquid material Substances 0.000 description 1
150000004668 long chain fatty acids Chemical class 0.000 description 1
238000003760 magnetic stirring Methods 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
230000000269 nucleophilic effect Effects 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
YTJSFYQNRXLOIC-UHFFFAOYSA-N octadecylsilane Chemical compound CCCCCCCCCCCCCCCCCC[SiH3] YTJSFYQNRXLOIC-UHFFFAOYSA-N 0.000 description 1
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
235000021313 oleic acid Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000746 purification Methods 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
241000894007 species Species 0.000 description 1
239000012086 standard solution Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000000185 sucrose group Chemical group 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
QHGNHLZPVBIIPX-UHFFFAOYSA-N tin(ii) oxide Chemical class [Sn]=O QHGNHLZPVBIIPX-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000001665 trituration Methods 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H11/00—Compounds containing saccharide radicals esterified by inorganic acids; Metal salts thereof
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/04—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals attached to acyclic carbon atoms
- C07H13/06—Fatty acids
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
- C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
- C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Saccharide Compounds (AREA)
Steroid Compounds (AREA)

IL9100489A 1988-07-18 1989-07-17 Regioselective synthesis of 1,3-DI-(6-O-sucrose)1,1,3,3-tetra (hydrocarbyl) distannoxane derivatives IL91004A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/220,641 US4950746A (en)	1988-07-18	1988-07-18	Process for synthesizing sucrose derivatives by regioselective reaction

Publications (2)

Publication Number	Publication Date
IL91004A0 IL91004A0 (en)	1990-02-09
IL91004A true IL91004A (en)	1994-04-12

Family

ID=22824357

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9100489A IL91004A (en)	1988-07-18	1989-07-17	Regioselective synthesis of 1,3-DI-(6-O-sucrose)1,1,3,3-tetra (hydrocarbyl) distannoxane derivatives

Country Status (24)

Country	Link
US (1)	US4950746A (fr)
EP (1)	EP0352048B1 (fr)
JP (1)	JP2725710B2 (fr)
KR (1)	KR0143234B1 (fr)
AR (1)	AR245136A1 (fr)
AT (1)	ATE114664T1 (fr)
AU (1)	AU618107B2 (fr)
CA (1)	CA1323625C (fr)
DE (1)	DE68919566T2 (fr)
DK (1)	DK170027B1 (fr)
ES (1)	ES2065386T3 (fr)
FI (1)	FI91874C (fr)
GR (1)	GR1002250B (fr)
IE (1)	IE65990B1 (fr)
IL (1)	IL91004A (fr)
MX (1)	MX172793B (fr)
NO (1)	NO171855C (fr)
NZ (1)	NZ229823A (fr)
PH (1)	PH26098A (fr)
PT (1)	PT91186B (fr)
RU (1)	RU2041233C1 (fr)
TR (1)	TR27628A (fr)
YU (1)	YU47159B (fr)
ZA (1)	ZA895427B (fr)

Families Citing this family (52)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5089608A (en) *	1990-03-23	1992-02-18	Mcneil-Ppc, Inc.	Selective 6-acylation of sucrose mediated by cyclic adducts of dialkyltin oxides and diols
US5034551A (en) *	1990-04-23	1991-07-23	Noramco, Inc.	Process for recovery of organotin esters from reaction mixtures containing the same and re-use of the recovered organotin compounds
US5023329A (en) *	1990-04-23	1991-06-11	Noramco, Inc.	Sucrose-6-ester production process
GR910100356A (el) *	1990-08-27	1992-08-31	Mcneil Ppc Inc	Καταλυόμενη μέ?οδος εστέρος-6-σακχαρόζης.
US5470969A (en) *	1990-08-27	1995-11-28	Mcneil-Ppc, Inc.	Catalyzed sucrose-6-ester process
FR2670493A1 (fr) *	1990-12-13	1992-06-19	Isochem Sa	Nouveaux composes monoesters du saccharose tels que les 2-0-acylsaccharoses et les 6-0-acylsaccharoses, ainsi que leurs procedes de synthese.
US5298611A (en) *	1993-03-12	1994-03-29	Mcneil-Ppc, Inc.	Sucralose pentaester production
US6608039B1 (en)	1994-07-11	2003-08-19	The United States Of America As Represented By The Secretary Of Agriculture	Chemically synthesized sugar esters for the control of soft-bodied arthropods
IL114551A0 (en)	1994-07-11	1995-11-27	Us Agriculture	Chemically synthesized sugar esters for the control of soft bodied arthropods
US5498709A (en)	1994-10-17	1996-03-12	Mcneil-Ppc, Inc.	Production of sucralose without intermediate isolation of crystalline sucralose-6-ester
DK0776903T3 (da)	1995-11-28	2003-05-12	Mcneil Ppc Inc	Fremgangsmåde til fremstilling af en saccharose-6-ester
US6121430A (en) *	1998-12-28	2000-09-19	University Of Iowa Research Foundation	Regiospecific synthesis of glucose-based surfactants
EP1339728B1 (fr) *	2000-11-17	2013-02-27	Tate & Lyle Technology Limited	Composition de sucralose amelioree et son procede de preparation
AU2002239550B2 (en)	2000-11-17	2006-11-16	Tate & Lyle Technology Limited	Meltable form of sucralose
US6890581B2 (en) *	2002-04-05	2005-05-10	Tate & Lyle Public Limited Company	Methods for buffer stabilized aqueous deacylation
US6943248B2 (en) *	2003-04-30	2005-09-13	Tate & Lyle Public Limited Company	Crystalline form of sucralose, and method for producing it
CN1176094C (zh) *	2003-05-23	2004-11-17	广东省食品工业研究所	一种三氯蔗糖的合成方法
US20050214425A1 (en) *	2004-03-23	2005-09-29	Roma Vazirani	Sugar substitute prepared with nutritive and high-intensity sweeteners
US20090105470A1 (en) *	2005-02-22	2009-04-23	Pharmed Medicare Private Limited , A Corporation	Tin Mediated Regioselective Synthesis of Sucrose-6-Esters
US7750146B2 (en)	2005-03-18	2010-07-06	Tate & Lyle Plc	Granular sucralose
US20060247180A1 (en) *	2005-04-29	2006-11-02	Bergey James L	Purgative composition and uses thereof
US20060276639A1 (en) *	2005-06-01	2006-12-07	Healthy Brands, Llc	Conversion of sucralose-6-ester to sucralose
CN100418976C (zh) *	2006-04-03	2008-09-17	广州科宏食品添加物有限公司	一种三氯蔗糖的制备方法
CN101092438A (zh) *	2006-06-22	2007-12-26	南京莱因医药科技有限公司	6－o－苯甲酰三氯半乳型蔗糖四乙酯的制备方法
GB0702854D0 (en) *	2007-01-09	2007-03-28	Tate & Lyle Plc	Method for the synthesis of sucrose-6-esters
GB0702857D0 (en) *	2007-01-19	2007-03-28	Tate & Lyle Plc	Improved sucralose production method
US20080227971A1 (en) *	2007-01-19	2008-09-18	Leinhos Duane A	Deacylation of sucralose-6-acylates
US20090076261A1 (en) *	2007-09-13	2009-03-19	Polymed Therapeutics, Inc.	Novel process for preparing sucrose-6-esters
CN101245085B (zh) *	2007-12-19	2012-02-01	上海同辰生物科技有限公司	一种三氯蔗糖的合成及纯化工艺
AR070082A1 (es) *	2008-01-04	2010-03-10	Tate & Lyle Technology Ltd	Metodo para la produccion de sucralosa
US7932380B2 (en)	2008-03-06	2011-04-26	Wanhe International (Group) Co. Ltd.	Process for the preparation of sucralose
US8557976B2 (en) *	2008-03-13	2013-10-15	Tate & Lyle Technology Limited	Microbial consortia and methods for their use
CN101977664B (zh) *	2008-03-20	2014-02-26	塔特和莱利技术有限公司	从叔酰胺溶剂中去除酸
US8436157B2 (en) *	2008-03-26	2013-05-07	Tate & Lyle Technology Limited	Method for the production of sucralose
US20090259036A1 (en) *	2008-04-03	2009-10-15	Tate & Lyle Technology Limited	Extraction of less polar impurities from sucralose containing aqueous feed streams
AR071134A1 (es) *	2008-04-03	2010-05-26	Tate & Lyle Technology Ltd	Cristalizacion de sucralosa a partir de chorros que contienen sucralosa
US8497367B2 (en) *	2008-04-03	2013-07-30	Tate & Lyle Technology Limited	Sucralose purification process
US20090299055A1 (en) *	2008-04-03	2009-12-03	Tate & Lyle Technology Limited	Purification of Sucralose Containing Feed Streams for Sucralose Crystallization
WO2009137193A2 (fr) *	2008-04-03	2009-11-12	Tate & Lyte Technology Ltd	Effet de la concentration d'hydrate de carbone sur l'efficacité de l'extraction de sucralose
GB2469157B (en)	2009-03-30	2011-07-06	John Kerr	Process for removing dimethylamine during sucralose production
GB2469158B (en)	2009-03-31	2011-09-28	Peter J Seaberg	Base-assisted formation of tin-sucrose adducts
GB2471348B (en)	2009-06-22	2011-12-14	Tate & Lyle Technology Ltd	A method for producing sucralose-6-acylate
GB2474310B (en)	2009-10-12	2012-02-29	Tate & Lyle Technology Ltd	Process for the production of sucrose-6-ester
GB2474311B (en) *	2009-10-12	2012-10-17	Tate & Lyle Technology Ltd	Low temperature, single solvent process for the production of sucrose-6-ester
CN101759728B (zh) *	2010-01-08	2012-01-11	江苏巨邦制药有限公司	三氯蔗糖的生产及精制方法
GB201110520D0 (en)	2011-05-10	2011-08-03	Tate & Lyle Technology Ltd	Extraction of carboxylic acids with tin compounds
CN105829332B (zh)	2013-12-16	2018-10-02	塔特和莱利技术有限公司	蔗糖-6-酯的氯化
GB2544217B (en)	2014-08-08	2020-03-25	Tate & Lyle Tech Ltd	Chlorination of sucrose-6-esters
GB2536480B (en)	2015-03-17	2019-09-04	Tate & Lyle Tech Ltd	DMF Distillation
WO2017091435A1 (fr)	2015-11-24	2017-06-01	Archer Daniels Midland Company	Oligomérisations de fdca et de glycols dans un procédé monotope d'estérification-transestérification catalysé par des acides de lewis organométalliques homogènes
GB2551591B (en)	2016-06-23	2019-08-07	Tate & Lyle Tech Ltd	Liquid-liquid extraction of DMF
WO2022051988A1 (fr)	2020-09-10	2022-03-17	安徽金禾实业股份有限公司	Procédé de préparation de sucrose-6-ester

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4435440A (en) *	1976-01-08	1984-03-06	Tate & Lyle Limited	Sweeteners
DE3065399D1 (en) *	1979-12-18	1983-11-24	Tate & Lyle Plc	Crystalline 4,1',6'-trichloro-4,1',6'-trideoxy-galactosucrose
DE3062467D1 (en) *	1979-12-20	1983-04-28	Tate & Lyle Plc	Process for the preparation of 4,1',6'-trichloro-4,1',6'-trideoxy-galactosucrose
ATE9355T1 (de) *	1980-07-08	1984-09-15	Tate & Lyle Public Limited Company	Verfahren zur herstellung von 4,1',6'-trichlor4,1',6'-trideoxygalactosucrose (tgs).

1988
- 1988-07-18 US US07/220,641 patent/US4950746A/en not_active Expired - Lifetime
1989
- 1989-07-04 NZ NZ229823A patent/NZ229823A/xx unknown
- 1989-07-12 AU AU38048/89A patent/AU618107B2/en not_active Expired
- 1989-07-12 YU YU139389A patent/YU47159B/sh unknown
- 1989-07-17 AR AR89314425A patent/AR245136A1/es active
- 1989-07-17 DK DK352689A patent/DK170027B1/da not_active IP Right Cessation
- 1989-07-17 ZA ZA895427A patent/ZA895427B/xx unknown
- 1989-07-17 JP JP1182762A patent/JP2725710B2/ja not_active Expired - Lifetime
- 1989-07-17 NO NO892926A patent/NO171855C/no not_active IP Right Cessation
- 1989-07-17 GR GR890100456A patent/GR1002250B/el not_active IP Right Cessation
- 1989-07-17 CA CA000605839A patent/CA1323625C/fr not_active Expired - Lifetime
- 1989-07-17 EP EP89307228A patent/EP0352048B1/fr not_active Expired - Lifetime
- 1989-07-17 DE DE68919566T patent/DE68919566T2/de not_active Expired - Lifetime
- 1989-07-17 AT AT89307228T patent/ATE114664T1/de not_active IP Right Cessation
- 1989-07-17 PT PT91186A patent/PT91186B/pt active IP Right Grant
- 1989-07-17 RU SU4614609/04A patent/RU2041233C1/ru not_active IP Right Cessation
- 1989-07-17 FI FI893455A patent/FI91874C/fi not_active IP Right Cessation
- 1989-07-17 IE IE231089A patent/IE65990B1/en not_active IP Right Cessation
- 1989-07-17 IL IL9100489A patent/IL91004A/en unknown
- 1989-07-17 ES ES89307228T patent/ES2065386T3/es not_active Expired - Lifetime
- 1989-07-18 TR TR00931/89A patent/TR27628A/xx unknown
- 1989-07-18 MX MX016842A patent/MX172793B/es unknown
- 1989-07-18 PH PH38957A patent/PH26098A/en unknown
- 1989-07-18 KR KR1019890010134A patent/KR0143234B1/ko not_active Expired - Fee Related

Also Published As

Publication number	Publication date
RU2041233C1 (ru)	1995-08-09
NO171855B (no)	1993-02-01
YU139389A (en)	1991-02-28
FI91874B (fi)	1994-05-13
KR0143234B1 (ko)	1998-07-01
FI893455A0 (fi)	1989-07-17
DE68919566D1 (de)	1995-01-12
IE65990B1 (en)	1995-11-29
PT91186B (pt)	1995-03-01
NZ229823A (en)	1991-01-29
MX172793B (es)	1994-01-13
EP0352048B1 (fr)	1994-11-30
ZA895427B (en)	1991-03-27
DK352689D0 (da)	1989-07-17
JP2725710B2 (ja)	1998-03-11
DE68919566T2 (de)	1995-04-13
IE892310L (en)	1990-01-18
AU3804889A (en)	1990-01-18
GR1002250B (en)	1996-04-23
KR910002884A (ko)	1991-02-26
GR890100456A (el)	1990-06-27
AU618107B2 (en)	1991-12-12
FI893455L (fi)	1990-01-19
US4950746A (en)	1990-08-21
ES2065386T3 (es)	1995-02-16
JPH0273096A (ja)	1990-03-13
AR245136A1 (es)	1993-12-30
IL91004A0 (en)	1990-02-09
MX16842A (es)	1993-04-01
EP0352048A2 (fr)	1990-01-24
YU47159B (sh)	1995-01-31
FI91874C (fi)	1994-08-25
PH26098A (en)	1992-02-06
EP0352048A3 (fr)	1991-09-04
NO171855C (no)	1993-05-12
ATE114664T1 (de)	1994-12-15
DK352689A (da)	1990-01-19
TR27628A (tr)	1995-06-14
DK170027B1 (da)	1995-05-01
NO892926D0 (no)	1989-07-17
NO892926L (no)	1990-01-19
CA1323625C (fr)	1993-10-26
PT91186A (pt)	1990-02-08

Legal Events

Date	Code	Title
1999-12-31	KB	Patent renewed
2003-09-17	KB	Patent renewed
2007-08-19	KB	Patent renewed

Publication	Publication Date	Title
US4950746A (en)	1990-08-21	Process for synthesizing sucrose derivatives by regioselective reaction
EP0454386B1 (fr)	1994-06-15	Procédé pour la production de sucrose-6-ester
US5089608A (en)	1992-02-18	Selective 6-acylation of sucrose mediated by cyclic adducts of dialkyltin oxides and diols
US8049002B2 (en)	2011-11-01	Processes for chemical synthesis of lipochitooligosaccharides
KR920004486B1 (ko)	1992-06-05	시토신 누클레오시드의 제조방법
EP0728763A1 (fr)	1996-08-28	Analogue de ganglioside gm3 dote d'un residu d'acide sialique fluore en position 9, et intermediaire necessaire
EP0389110B1 (fr)	1995-05-03	Procédé pour préparer la 2'-déoxy-5-trifluorméthyl-ss-uridine
MX2007010241A (es)	2007-11-07	Sintesis regioselectiva mediada por estano de 6-esteres de sacarosa.
CA1269660A (fr)	1990-05-29	Preparation de fluorures de glucosyle proteges a l'oxygene
US5712387A (en)	1998-01-27	High yield stereospecific mannosylation
IE46989B1 (en)	1983-11-16	Process for preparing gold compounds
US4600771A (en)	1986-07-15	Process for the preparation of acylated sugars with a glycosidically bonded isothiocyanate group
EP0114331B1 (fr)	1987-05-20	Procédé pour la préparation d'oxanosine
EP0373919A2 (fr)	1990-06-20	Procédé de préparation de 2'-déoxy-bêta-adénosine