CA2100821C - Glucosidation avec controle de la stereospecificite - Google Patents

Glucosidation avec controle de la stereospecificite Download PDF

Info

Publication number: CA2100821C
Authority: CA; Canada
Prior art keywords: carbon atoms; group; alkoxy; arylalkoxy; solvent
Prior art date: 1993-07-19
Legal status (The legal status 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 status listed.): Expired - Lifetime

Application number

CA002100821A

Other languages

English (en)

Other versions

CA2100821A1 (fr

Inventor

Stephen Hanessian

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Individual

Original Assignee

Individual

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.)

1993-07-19

Filing date

1993-07-19

Publication date

2001-01-16

1993-07-19 Application filed by Individual filed Critical Individual

1993-07-19 Priority to CA002100821A priority Critical patent/CA2100821C/fr

1994-07-19 Priority to AU72620/94A priority patent/AU7262094A/en

1994-07-19 Priority to PCT/CA1994/000396 priority patent/WO1995003316A2/fr

1994-07-19 Priority to US08/403,813 priority patent/US5767256A/en

1995-01-20 Publication of CA2100821A1 publication Critical patent/CA2100821A1/fr

2001-01-16 Application granted granted Critical

2001-01-16 Publication of CA2100821C publication Critical patent/CA2100821C/fr

2013-07-19 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000005858 glycosidation reaction Methods 0.000 title description 2
229930182470 glycoside Natural products 0.000 claims abstract description 104
150000002338 glycosides Chemical class 0.000 claims abstract description 79
238000003786 synthesis reaction Methods 0.000 claims abstract description 33
239000002777 nucleoside Substances 0.000 claims abstract description 18
125000004432 carbon atom Chemical group C* 0.000 claims description 356
125000003545 alkoxy group Chemical group 0.000 claims description 92
239000002904 solvent Substances 0.000 claims description 76
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 74
238000000034 method Methods 0.000 claims description 72
239000000370 acceptor Substances 0.000 claims description 71
230000008569 process Effects 0.000 claims description 70
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 66
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 65
125000004423 acyloxy group Chemical group 0.000 claims description 52
OIRDBPQYVWXNSJ-UHFFFAOYSA-N methyl trifluoromethansulfonate Chemical group COS(=O)(=O)C(F)(F)F OIRDBPQYVWXNSJ-UHFFFAOYSA-N 0.000 claims description 50
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 42
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 40
239000000203 mixture Substances 0.000 claims description 36
-1 trialkylsilyl ethers Chemical class 0.000 claims description 34
SBTSVTLGWRLWOD-UHFFFAOYSA-L copper(ii) triflate Chemical compound [Cu+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F SBTSVTLGWRLWOD-UHFFFAOYSA-L 0.000 claims description 33
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 30
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 30
230000015572 biosynthetic process Effects 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 24
238000006243 chemical reaction Methods 0.000 claims description 23
229910052739 hydrogen Inorganic materials 0.000 claims description 22
239000001257 hydrogen Substances 0.000 claims description 22
230000001476 alcoholic effect Effects 0.000 claims description 21
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims description 18
WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 claims description 16
239000002841 Lewis acid Substances 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 15
150000007517 lewis acids Chemical class 0.000 claims description 15
125000005389 trialkylsiloxy group Chemical group 0.000 claims description 15
239000011592 zinc chloride Substances 0.000 claims description 15
235000005074 zinc chloride Nutrition 0.000 claims description 15
JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 claims description 15
150000002431 hydrogen Chemical class 0.000 claims description 14
230000006872 improvement Effects 0.000 claims description 14
239000002184 metal Substances 0.000 claims description 14
229910052751 metal Inorganic materials 0.000 claims description 14
150000002739 metals Chemical class 0.000 claims description 14
QRUBYZBWAOOHSV-UHFFFAOYSA-M silver trifluoromethanesulfonate Chemical compound [Ag+].[O-]S(=O)(=O)C(F)(F)F QRUBYZBWAOOHSV-UHFFFAOYSA-M 0.000 claims description 14
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 12
230000008878 coupling Effects 0.000 claims description 12
238000010168 coupling process Methods 0.000 claims description 12
238000005859 coupling reaction Methods 0.000 claims description 12
150000007513 acids Chemical class 0.000 claims description 11
FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical group C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 claims description 11
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
125000004442 acylamino group Chemical group 0.000 claims description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
150000003833 nucleoside derivatives Chemical class 0.000 claims description 8
150000002148 esters Chemical class 0.000 claims description 7
125000000623 heterocyclic group Chemical group 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 7
239000011347 resin Substances 0.000 claims description 7
229920005989 resin Polymers 0.000 claims description 7
229910052717 sulfur Inorganic materials 0.000 claims description 7
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 6
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 6
125000004665 trialkylsilyl group Chemical group 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000003302 alkenyloxy group Chemical group 0.000 claims description 4
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 3
239000007800 oxidant agent Substances 0.000 claims description 3
150000003212 purines Chemical class 0.000 claims description 3
125000001424 substituent group Chemical group 0.000 claims description 3
BHSZFCYZAUSCLC-UHFFFAOYSA-N (6-aminopurin-6-yl)-phenylmethanone Chemical group N1=CN=C2N=CN=C2C1(N)C(=O)C1=CC=CC=C1 BHSZFCYZAUSCLC-UHFFFAOYSA-N 0.000 claims description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
125000001142 dicarboxylic acid group Chemical group 0.000 claims description 2
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 36
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 claims 14
125000000837 carbohydrate group Chemical group 0.000 claims 1
239000002773 nucleotide Substances 0.000 claims 1
125000003729 nucleotide group Chemical group 0.000 claims 1
150000002016 disaccharides Chemical class 0.000 abstract description 29
238000002360 preparation method Methods 0.000 abstract description 9
150000001875 compounds Chemical class 0.000 abstract description 8
229920001542 oligosaccharide Polymers 0.000 abstract description 8
150000002482 oligosaccharides Chemical class 0.000 abstract description 8
125000003835 nucleoside group Chemical group 0.000 abstract description 5
150000004043 trisaccharides Chemical class 0.000 abstract description 3
229920000642 polymer Polymers 0.000 abstract description 2
IUIQMWSJNSOELI-UHFFFAOYSA-N (4-methoxy-3-pyridin-2-yloxypyridin-2-yl) hydrogen carbonate Chemical compound COC1=C(C(=NC=C1)OC(=O)O)OC2=CC=CC=N2 IUIQMWSJNSOELI-UHFFFAOYSA-N 0.000 abstract 1
125000004076 pyridyl group Chemical group 0.000 abstract 1
125000005554 pyridyloxy group Chemical group 0.000 abstract 1
239000000386 donor Substances 0.000 description 58
239000010949 copper Substances 0.000 description 28
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 22
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 12
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
125000005640 glucopyranosyl group Chemical group 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
230000004913 activation Effects 0.000 description 6
125000003147 glycosyl group Chemical group 0.000 description 6
239000002243 precursor Substances 0.000 description 6
238000011161 development Methods 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
230000035484 reaction time Effects 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
150000001720 carbohydrates Chemical class 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Chemical compound NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 description 4
NRNCYVBFPDDJNE-UHFFFAOYSA-N pemoline Chemical compound O1C(N)=NC(=O)C1C1=CC=CC=C1 NRNCYVBFPDDJNE-UHFFFAOYSA-N 0.000 description 4
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
238000013459 approach Methods 0.000 description 3
235000014633 carbohydrates Nutrition 0.000 description 3
150000001721 carbon Chemical group 0.000 description 3
230000008859 change Effects 0.000 description 3
238000012360 testing method Methods 0.000 description 3
RWQNBRDOKXIBIV-UHFFFAOYSA-N thymine Chemical class CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 description 3
ZNKMCQRFDSVZAX-DFLSAPQXSA-N (2r,3r,4s,5r,6s)-6-methoxy-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)oxan-3-ol Chemical compound C([C@H]1O[C@@H]([C@@H]([C@@H](OCC=2C=CC=CC=2)[C@@H]1O)OCC=1C=CC=CC=1)OC)OCC1=CC=CC=C1 ZNKMCQRFDSVZAX-DFLSAPQXSA-N 0.000 description 2
HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 2
ISAKRJDGNUQOIC-UHFFFAOYSA-N Uracil Chemical compound O=C1C=CNC(=O)N1 ISAKRJDGNUQOIC-UHFFFAOYSA-N 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
239000012190 activator Substances 0.000 description 2
239000004106 carminic acid Substances 0.000 description 2
230000003197 catalytic effect Effects 0.000 description 2
HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
229940104302 cytosine Drugs 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000002337 glycosamines Chemical class 0.000 description 2
238000007689 inspection Methods 0.000 description 2
230000007246 mechanism Effects 0.000 description 2
230000004048 modification Effects 0.000 description 2
238000012986 modification Methods 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
125000003132 pyranosyl group Chemical group 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000002718 pyrimidine nucleoside Substances 0.000 description 2
230000009257 reactivity Effects 0.000 description 2
WQZGKKKJIJFFOK-SVZMEOIVSA-N (+)-Galactose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-SVZMEOIVSA-N 0.000 description 1
VEIMZMGQUXYRIR-HNNXBMFYSA-N (2s)-2-[benzoyl(benzyl)amino]-3-hydroxypropanoic acid Chemical compound C=1C=CC=CC=1C(=O)N([C@@H](CO)C(O)=O)CC1=CC=CC=C1 VEIMZMGQUXYRIR-HNNXBMFYSA-N 0.000 description 1
LDERFNFRJLQIAC-LBPRGKRZSA-N (2s)-2-[benzyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-3-hydroxypropanoic acid Chemical compound CC(C)(C)OC(=O)N([C@@H](CO)C(O)=O)CC1=CC=CC=C1 LDERFNFRJLQIAC-LBPRGKRZSA-N 0.000 description 1
LIUIQRUWBMHCQV-UHFFFAOYSA-N 1-trimethylsilylpyrimidine-2,4-dione Chemical compound C[Si](C)(C)N1C=CC(=O)NC1=O LIUIQRUWBMHCQV-UHFFFAOYSA-N 0.000 description 1
WCASXYBKJHWFMY-NSCUHMNNSA-N 2-Buten-1-ol Chemical compound C\C=C\CO WCASXYBKJHWFMY-NSCUHMNNSA-N 0.000 description 1
QYBKTVCUGGRXTH-UHFFFAOYSA-N 5-(trimethylsilylmethyl)-1H-pyrimidine-2,4-dione Chemical compound C[Si](C)(C)CC=1C(NC(NC=1)=O)=O QYBKTVCUGGRXTH-UHFFFAOYSA-N 0.000 description 1
VWXGRWMELBPMCU-UHFFFAOYSA-N 5-chloro-1-[3-(dimethylamino)propyl]-3-phenylbenzimidazol-2-one Chemical compound O=C1N(CCCN(C)C)C2=CC=C(Cl)C=C2N1C1=CC=CC=C1 VWXGRWMELBPMCU-UHFFFAOYSA-N 0.000 description 1
208000030507 AIDS Diseases 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
235000016936 Dendrocalamus strictus Nutrition 0.000 description 1
QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
241001175904 Labeo bata Species 0.000 description 1
125000003686 N-acetyl-D-glucosaminyl group Chemical group C(C)(=O)N[C@H]1C(O[C@@H]([C@H]([C@@H]1O)O)CO)* 0.000 description 1
XDMCWZFLLGVIID-SXPRBRBTSA-N O-(3-O-D-galactosyl-N-acetyl-beta-D-galactosaminyl)-L-serine Chemical compound CC(=O)N[C@H]1[C@H](OC[C@H]([NH3+])C([O-])=O)O[C@H](CO)[C@H](O)[C@@H]1OC1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 XDMCWZFLLGVIID-SXPRBRBTSA-N 0.000 description 1
KUIFHYPNNRVEKZ-VIJRYAKMSA-N O-(N-acetyl-alpha-D-galactosaminyl)-L-threonine Chemical compound OC(=O)[C@@H](N)[C@@H](C)O[C@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1NC(C)=O KUIFHYPNNRVEKZ-VIJRYAKMSA-N 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000534944 Thia Species 0.000 description 1
OBVFJYUDIWPVKD-HENWMNBSSA-N [(2r,3r,4s,5r)-4,5-diacetyloxy-2-(hydroxymethyl)-6-methoxyoxan-3-yl] acetate Chemical compound COC1O[C@H](CO)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O OBVFJYUDIWPVKD-HENWMNBSSA-N 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
BLAKAEFIFWAFGH-UHFFFAOYSA-N acetyl acetate;pyridine Chemical compound C1=CC=NC=C1.CC(=O)OC(C)=O BLAKAEFIFWAFGH-UHFFFAOYSA-N 0.000 description 1
230000021736 acetylation Effects 0.000 description 1
238000006640 acetylation reaction Methods 0.000 description 1
125000003550 alpha-D-galactosyl group Chemical group C1([C@H](O)[C@@H](O)[C@@H](O)[C@H](O1)CO)* 0.000 description 1
WQZGKKKJIJFFOK-UHFFFAOYSA-N alpha-D-glucopyranose Natural products OCC1OC(O)C(O)C(O)C1O WQZGKKKJIJFFOK-UHFFFAOYSA-N 0.000 description 1
230000004075 alteration Effects 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
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000012000 cholesterol Nutrition 0.000 description 1
230000009918 complex formation Effects 0.000 description 1
150000004696 coordination complex Chemical class 0.000 description 1
230000002596 correlated effect Effects 0.000 description 1
HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
239000000348 glycosyl donor Substances 0.000 description 1
150000002373 hemiacetals Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
238000012804 iterative process Methods 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
ORMNPSYMZOGSSV-UHFFFAOYSA-N mercury(II) nitrate Inorganic materials [Hg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ORMNPSYMZOGSSV-UHFFFAOYSA-N 0.000 description 1
UYWUMFGDPBMNCA-UHFFFAOYSA-N methyl beta-D-glucopyranoside tetra-O-acetate Natural products COC1OC(COC(C)=O)C(OC(C)=O)C(OC(C)=O)C1OC(C)=O UYWUMFGDPBMNCA-UHFFFAOYSA-N 0.000 description 1
AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
150000002918 oxazolines Chemical class 0.000 description 1
UFGTXPLSPACVGS-UHFFFAOYSA-N pyridin-2-yl hydrogen carbonate Chemical group OC(=O)OC1=CC=CC=N1 UFGTXPLSPACVGS-UHFFFAOYSA-N 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
229940113082 thymine Drugs 0.000 description 1
QNALEQFOLRRVQI-UHFFFAOYSA-N trimethyl(pyrimidin-2-yl)silane Chemical compound C[Si](C)(C)C1=NC=CC=N1 QNALEQFOLRRVQI-UHFFFAOYSA-N 0.000 description 1
229940035893 uracil Drugs 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1
150000008501 α-D-glucopyranosides Chemical class 0.000 description 1
150000008135 α-glycosides Chemical class 0.000 description 1
150000008136 β-glycosides Chemical class 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms

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)

CA002100821A 1993-07-19 1993-07-19 Glucosidation avec controle de la stereospecificite Expired - Lifetime CA2100821C (fr)

Priority Applications (4)

Application Number	Priority Date	Filing Date	Title
CA002100821A CA2100821C (fr)	1993-07-19	1993-07-19	Glucosidation avec controle de la stereospecificite
AU72620/94A AU7262094A (en)	1993-07-19	1994-07-19	Solution and solid phase stereocontrolled glycosidation
PCT/CA1994/000396 WO1995003316A2 (fr)	1993-07-19	1994-07-19	Glycosidation stereoregulee en phase solide et en solution
US08/403,813 US5767256A (en)	1993-07-19	1994-07-19	Solution and solid phase stereocontrolled glycosidation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA002100821A CA2100821C (fr)	1993-07-19	1993-07-19	Glucosidation avec controle de la stereospecificite

Publications (2)

Publication Number	Publication Date
CA2100821A1 CA2100821A1 (fr)	1995-01-20
CA2100821C true CA2100821C (fr)	2001-01-16

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Application Number	Title	Priority Date	Filing Date
CA002100821A Expired - Lifetime CA2100821C (fr)	1993-07-19	1993-07-19	Glucosidation avec controle de la stereospecificite

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CA (1)	CA2100821C (fr)
WO (1)	WO1995003316A2 (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP1440077B1 (fr) *	2001-09-07	2013-05-01	Alchemia Limited	Pentasaccharides hepariniques synthetiques
WO2013091660A1 (fr) *	2011-12-23	2013-06-27	Glycom A/S	Procédé pour obtenir des précurseurs de lacto-n-tétraose et de lacto-n-neotétraose cristallin et des mélanges de ceux-ci
EP3013365B1 (fr) *	2013-06-26	2019-06-05	Academia Sinica	Antigènes rm2 et leur utilisation
KR101639160B1 (ko) *	2015-06-10	2016-07-12	건국대학교 산학협력단	메틸 바이올렛 염료 제거용 벤질 트리아졸 덱스트란 유도체
CN113926472B (zh) *	2021-07-29	2022-10-18	山东大学	一种糖苷化反应催化剂、糖苷化方法和应用

1993
- 1993-07-19 CA CA002100821A patent/CA2100821C/fr not_active Expired - Lifetime
1994
- 1994-07-19 WO PCT/CA1994/000396 patent/WO1995003316A2/fr not_active Ceased

Also Published As

Publication number	Publication date
CA2100821A1 (fr)	1995-01-20
WO1995003316A3 (fr)	1995-03-30
WO1995003316A2 (fr)	1995-02-02

Legal Events

Date	Code	Title	Description
1996-04-24	EEER	Examination request
2023-05-26	MKEX	Expiry	Effective date: 20130719

Publication	Publication Date	Title
Murakata et al.	1992	Stereoselective total synthesis of the glycosyl phosphatidylinositol (GPI) anchor of Trypanosoma brucei
Pozsgay et al.	1988	Synthetic oligosaccharides related to group B streptococcal polysaccharides. 3. Synthesis of oligosaccharides corresponding to the common polysaccharide antigen of group B streptococci
JPH0225498A (ja)	1990-01-26	新規なα‐グルコシダーゼ抑制剤
Boons et al.	1992	Synthesis of LD-Hepp and KDO containing di-and tetrasaccharide derivatives of Neisseria meningitidis inner-core region via iodonium ion promoted glycosidations
Sherman et al.	2001	Synthesis of Neu5Ac-and Neu5Gc-α-(2→ 6′)-lactosamine 3-aminopropyl glycosides
Ennis et al.	2001	N-Iodosuccinimide-mediated intramolecular aglycon delivery
CA2100821C (fr)	2001-01-16	Glucosidation avec controle de la stereospecificite
Yamanoi et al.	1994	New Synthetic Methods and Reagents for Complex Carbohydrates. VIII. Stereoselective. ALPHA.-and. BETA.-Mannopyranoside Formation from Glycosyl Dimethylphosphinothioates with the C-2 Axial Benzyloxyl Group.
US5097023A (en)	1992-03-17	α-glucosidase inhibitors
Barili et al.	1997	Improved preparation of 2, 3: 5, 6: 3′, 4′-tri-O-isopropylidenelactose dimethyl acetal and its 6′-O-(1-methoxy-1-methylethyl) derivative
Lafont et al.	1997	A convenient access to β-glycosides of N-acetyllactosamine
Allanson et al.	1994	The synthesis of novel mimics of the sialyl Lewis x determinant
US5854408A (en)	1998-12-29	Process for acylating the 1-position of saccharides
EP0255717A2 (fr)	1988-02-10	Dérivés de gangliosides et leur procédé de préparation
Hernández-Torres et al.	2002	Optimized synthesis of an orthogonally protected glucosamine
St-Pierre et al.	2016	Stereocontrolled synthesis of phenolic α-D-glycopyranosides
Bugianesi et al.	1971	A chemical synthesis of IO-indomethacin-β-D-glucosyluronic acid
JP3136491B2 (ja)	2001-02-19	新規なα―グルコシダーゼ抑制剤
Alais et al.	1987	Synthesis of an octasaccharide fragment of the polylactosamine series by a blockwise approach
JPS6136294A (ja)	1986-02-20	弗化グリコシルからのグリコサイドの製造方法
Miquel et al.	2004	Efficient synthesis of O-, S-, N-and C-glycosides of 2-amino-2-deoxy-D-glucopyranose from glycosyl iodides
Sheerin et al.	2017	Large scale synthesis and regioselective protection schemes of ethyl 2-azido-2-deoxy-1-thio-α-d-cellobioside for preparation of heparin thiodisaccharide building blocks
Wang et al.	1988	Synthesis of fragments of the capsular polysaccharide of haemophilus influenzae type B
JPH02268154A (ja)	1990-11-01	新規なα―グルコシダーゼ抑制剤
Zegelaar-Jaarsveld et al.	1996	Iodonium ion-assisted synthesis of a tetrameric fragment corresponding to the cell wall phenolic glycolipids of Mycobacterium kansasii serovar I