DK169257B1 - Fremgangsmåde til fremstilling af sucralose - Google Patents

Fremgangsmåde til fremstilling af sucralose Download PDF

Info

Publication number: DK169257B1
Authority: DK; Denmark
Prior art keywords: pas; chloride; acetylsaccharose; penta; trispa
Prior art date: 1986-09-17

Application number

DK487087A

Other languages

Danish (da)

English (en)

Other versions

DK487087A (da

DK487087D0 (da

Inventor

George Henry Sankey

Nigel John Homer

Original Assignee

Tate & Lyle Plc

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.)

1986-09-17

Filing date

1987-09-16

Publication date

1994-09-26

1987-09-16 Application filed by Tate & Lyle Plc filed Critical Tate & Lyle Plc

1987-09-16 Publication of DK487087D0 publication Critical patent/DK487087D0/da

1988-03-18 Publication of DK487087A publication Critical patent/DK487087A/da

1994-09-26 Application granted granted Critical

1994-09-26 Publication of DK169257B1 publication Critical patent/DK169257B1/da

Links

239000004376 Sucralose Substances 0.000 title claims abstract description 23
BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 title claims abstract description 23
235000019408 sucralose Nutrition 0.000 title claims abstract description 23
238000000034 method Methods 0.000 title claims description 32
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 22
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims abstract description 18
229910000041 hydrogen chloride Inorganic materials 0.000 claims abstract description 18
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims abstract description 17
239000003054 catalyst Substances 0.000 claims abstract description 14
238000002360 preparation method Methods 0.000 claims abstract description 14
238000007327 hydrogenolysis reaction Methods 0.000 claims abstract description 13
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims abstract description 13
-1 aralkyl chloride Chemical compound 0.000 claims abstract description 12
125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 9
230000003197 catalytic effect Effects 0.000 claims abstract description 8
229910052763 palladium Inorganic materials 0.000 claims abstract description 7
239000003960 organic solvent Substances 0.000 claims abstract description 6
229910052697 platinum Inorganic materials 0.000 claims abstract description 6
229930006000 Sucrose Natural products 0.000 claims abstract description 3
239000005720 sucrose Substances 0.000 claims abstract description 3
AHLIHMGXFJRKSY-ZQNATQRZSA-N [(2r,3r,4s,5r,6r)-4,5-diacetyloxy-6-[(2s,3s,4r,5r)-3,4-diacetyloxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxyoxan-2-yl]methyl acetate Chemical compound CC(=O)O[C@@H]1[C@@H](OC(C)=O)[C@H](O)[C@@H](COC(=O)C)O[C@@H]1O[C@@]1(CO)[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@@H](CO)O1 AHLIHMGXFJRKSY-ZQNATQRZSA-N 0.000 claims description 27
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical group C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 claims description 16
238000006243 chemical reaction Methods 0.000 claims description 15
239000000203 mixture Substances 0.000 claims description 12
238000006317 isomerization reaction Methods 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 claims description 5
229940073608 benzyl chloride Drugs 0.000 claims description 4
238000005660 chlorination reaction Methods 0.000 claims description 4
238000002955 isolation Methods 0.000 claims description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
150000008282 halocarbons Chemical group 0.000 claims description 3
230000006196 deacetylation Effects 0.000 claims description 2
238000003381 deacetylation reaction Methods 0.000 claims description 2
238000000746 purification Methods 0.000 claims description 2
UMOFHQSJMUINFR-UHFFFAOYSA-N [4,5-diacetyloxy-6-[3,4-diacetyloxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy-2-(hydroxymethyl)oxan-3-yl] acetate Chemical compound CC(=O)OC1C(OC(=O)C)C(CO)OC1(CO)OC1C(OC(C)=O)C(OC(C)=O)C(OC(C)=O)C(CO)O1 UMOFHQSJMUINFR-UHFFFAOYSA-N 0.000 abstract 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 51
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
239000000047 product Substances 0.000 description 11
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
229960000583 acetic acid Drugs 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000006642 detritylation reaction Methods 0.000 description 5
239000007858 starting material Substances 0.000 description 5
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000002253 acid Substances 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
239000007787 solid Substances 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
239000007789 gas Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
238000003556 assay Methods 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
230000015556 catabolic process Effects 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
239000012362 glacial acetic acid Substances 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000012485 toluene extract Substances 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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 description 1
150000007513 acids Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
238000009835 boiling Methods 0.000 description 1
150000001720 carbohydrates Chemical class 0.000 description 1
238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
238000010531 catalytic reduction reaction Methods 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229920001429 chelating resin Polymers 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003245 coal Substances 0.000 description 1
150000001875 compounds Chemical class 0.000 description 1
239000000470 constituent Substances 0.000 description 1
238000011109 contamination Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000012043 crude product Substances 0.000 description 1
238000006073 displacement reaction Methods 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000008123 high-intensity sweetener Substances 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
229910000042 hydrogen bromide Inorganic materials 0.000 description 1
229910000039 hydrogen halide Inorganic materials 0.000 description 1
239000012433 hydrogen halide Substances 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
238000006386 neutralization reaction Methods 0.000 description 1
235000013615 non-nutritive sweetener Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
231100000572 poisoning Toxicity 0.000 description 1
230000000607 poisoning effect Effects 0.000 description 1
230000002035 prolonged effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000000758 substrate Substances 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 1
FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
- C07H15/06—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical being a hydroxyalkyl group esterified by a fatty acid
- 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Molecular Biology (AREA)
Life Sciences & Earth Sciences (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Crystallography & Structural Chemistry (AREA)
Saccharide Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Catalysts (AREA)
Steroid Compounds (AREA)
Glass Compositions (AREA)
Iron Core Of Rotating Electric Machines (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DK487087A 1986-09-17 1987-09-16 Fremgangsmåde til fremstilling af sucralose DK169257B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8622342		1986-09-17
GB868622342A GB8622342D0 (en)	1986-09-17	1986-09-17	Process

Publications (3)

Publication Number	Publication Date
DK487087D0 DK487087D0 (da)	1987-09-16
DK487087A DK487087A (da)	1988-03-18
DK169257B1 true DK169257B1 (da)	1994-09-26

Family

ID=10604300

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK487087A DK169257B1 (da)	1986-09-17	1987-09-16	Fremgangsmåde til fremstilling af sucralose

Country Status (13)

Country	Link
US (1)	US4920207A (de)
EP (1)	EP0260978B1 (de)
JP (1)	JPH0778071B2 (de)
KR (1)	KR880003967A (de)
AT (1)	ATE55607T1 (de)
CA (1)	CA1300132C (de)
DE (1)	DE3764335D1 (de)
DK (1)	DK169257B1 (de)
ES (1)	ES2016847B3 (de)
GB (2)	GB8622342D0 (de)
GR (1)	GR3000781T3 (de)
IE (1)	IE61064B1 (de)
PT (1)	PT85744B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2663815A1 (fr) *	1990-06-27	1992-01-03	Montpellier Ii Universite	Composition et application comme agent antiappetant d'esters de saccharose.
US5122601A (en) *	1990-12-07	1992-06-16	Hawaiian Sugar Planters'association	Synthesis of 2,3,3',4,4'-penta-o-methylsucrose
US6943248B2 (en) *	2003-04-30	2005-09-13	Tate & Lyle Public Limited Company	Crystalline form of sucralose, and method for producing it
CN100415762C (zh) *	2006-08-28	2008-09-03	江南大学	一种合成三氯蔗糖的中间体的制备方法
BRPI0719916A2 (pt) *	2006-12-05	2014-03-04	Tate & Lyle Technology Ltd	Recuperação de cloreto de tritila

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
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
GB8525953D0 (en) *	1985-10-21	1985-11-27	Mcneilab Inc	Preparation of galactopyranoside

1986
- 1986-09-17 GB GB868622342A patent/GB8622342D0/en active Pending
1987
- 1987-09-16 CA CA000547019A patent/CA1300132C/en not_active Expired - Fee Related
- 1987-09-16 IE IE250887A patent/IE61064B1/en not_active IP Right Cessation
- 1987-09-16 DK DK487087A patent/DK169257B1/da not_active IP Right Cessation
- 1987-09-17 GB GB08721854A patent/GB2195335A/en not_active Withdrawn
- 1987-09-17 DE DE8787308259T patent/DE3764335D1/de not_active Expired - Fee Related
- 1987-09-17 EP EP87308259A patent/EP0260978B1/de not_active Expired - Lifetime
- 1987-09-17 JP JP62233625A patent/JPH0778071B2/ja not_active Expired - Lifetime
- 1987-09-17 KR KR870010327A patent/KR880003967A/ko not_active Abandoned
- 1987-09-17 ES ES87308259T patent/ES2016847B3/es not_active Expired - Lifetime
- 1987-09-17 PT PT85744A patent/PT85744B/pt not_active IP Right Cessation
- 1987-09-17 AT AT87308259T patent/ATE55607T1/de not_active IP Right Cessation
- 1987-09-17 US US07/098,023 patent/US4920207A/en not_active Expired - Fee Related
1990
- 1990-09-12 GR GR90400639T patent/GR3000781T3/el unknown

Also Published As

Publication number	Publication date
GB8622342D0 (en)	1986-10-22
EP0260978A3 (en)	1988-12-14
JPH0778071B2 (ja)	1995-08-23
EP0260978B1 (de)	1990-08-16
JPS63165395A (ja)	1988-07-08
ATE55607T1 (de)	1990-09-15
IE61064B1 (en)	1994-09-21
US4920207A (en)	1990-04-24
DE3764335D1 (de)	1990-09-20
GB8721854D0 (en)	1987-10-21
PT85744B (pt)	1990-07-31
DK487087A (da)	1988-03-18
DK487087D0 (da)	1987-09-16
GR3000781T3 (en)	1991-10-10
CA1300132C (en)	1992-05-05
PT85744A (en)	1987-10-01
EP0260978A2 (de)	1988-03-23
IE872508L (en)	1988-03-17
GB2195335A (en)	1988-04-07
ES2016847B3 (es)	1990-12-01
KR880003967A (ko)	1988-05-31

Legal Events

Date	Code	Title	Description
1994-09-26	B1	Patent granted (law 1993)
1996-05-20	PBP	Patent lapsed

Publication	Publication Date	Title
JP3140775B2 (ja)	2001-03-05	ラムノリピドからラムノースを製造する方法
EP2828275B1 (de)	2017-03-01	Synthese von trisaccharid 3-o-fucosyllactose und zwischenprodukte davon
CA2114180C (en)	1997-11-25	Sucralose pentaester production
US6049004A (en)	2000-04-11	Nitric acid removal from oxidation products
US20030097029A1 (en)	2003-05-22	Process for the production of xylitol
Lipták et al.	1980	Synthesis and 13C-NMR spectroscopic investigations of rhamnobioses
JP3751670B2 (ja)	2006-03-01	キシリトールの生成方法
KR830001842B1 (ko)	1983-09-14	5'-데옥시-5-플루오로우리딘의 제법
JP2000157300A (ja)	2000-06-13	アラビノキシラン含有材料からのポリオ―ルの製造方法
DK169257B1 (da)	1994-09-26	Fremgangsmåde til fremstilling af sucralose
DK159851B (da)	1990-12-17	Fremgangsmaade til fremstilling af riboflavin
DK158472B (da)	1990-05-21	Saccharosederivater, fremgangsmaade til fremstilling deraf og disses anvendelse som soedemidler
US5433793A (en)	1995-07-18	Preparation of high purity D-allose from D-glucose
JP5612603B2 (ja)	2014-10-22	ベータ−アセチルフラノシドの回収方法
US2922783A (en)	1960-01-26	Preparation of sugar derivatives
NO300638B1 (no)	1997-06-30	Ny og forbedret opplösningsmiddelfri syntese av etersubstituerte, blokkerte monosakkarider og deres selektive hydrolyse
Franzyk et al.	1998	Ozonolysis of protected iridoid glucosides
Fang et al.	1987	Synthesis of Substituted 2, 6-Dioxabicyclo [3.1. 1] Heptanes: 1, 3-Anhydro-2, 4-DI-O-Benzyl and 1, 3-Anhydrq-2, 4-DI-O-(p-Bromobenzyl)-β-D-Rhamnopyranose
JPH0547554B2 (de)	1993-07-19
Sakairi et al.	1983	Synthesis of a 4′-amino-4′, 6′-dideoxymaltose derivative as a synthon of an α-d-glucosidase inhibitor
US5550227A (en)	1996-08-27	Method for the preparation of rhamnose monohydrate from rhamnolipids
Tsujino	1963	Studies on Alginase Part III. Constitution of a New Unsaturated Diuronide
Hirsch et al.	1973	Easy route to 2-O-substituted D-xylose derivatives
JPH04149189A (ja)	1992-05-22	Ｄ―アルトロースの製造方法
JP2005539032A (ja)	2005-12-22	リボフラノースの製造方法