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WO2005121114A3 - 1,5 and 1,4-anhydroketoses, methods for the preparation of 1,5-and 1,4-anhydroketoses, intermediates, and uses of 1,5-and 1,4-anhydroketoses - Google Patents

1,5 and 1,4-anhydroketoses, methods for the preparation of 1,5-and 1,4-anhydroketoses, intermediates, and uses of 1,5-and 1,4-anhydroketoses Download PDF

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Publication number
WO2005121114A3
WO2005121114A3 PCT/DK2005/000377 DK2005000377W WO2005121114A3 WO 2005121114 A3 WO2005121114 A3 WO 2005121114A3 DK 2005000377 W DK2005000377 W DK 2005000377W WO 2005121114 A3 WO2005121114 A3 WO 2005121114A3
Authority
WO
WIPO (PCT)
Prior art keywords
anhydroketoses
anhydro
preparation
deprotection
methods
Prior art date
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.)
Ceased
Application number
PCT/DK2005/000377
Other languages
French (fr)
Other versions
WO2005121114A2 (en
Inventor
Inge Lundt
Arnold Stuetz
Gyula Dekany
Joachim Thiem
Karoly Agoston
Mikkel Andreassen
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.)
Glycom AS
Original Assignee
Glycom AS
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.)
Filing date
Publication date
Priority claimed from AU2004903036A external-priority patent/AU2004903036A0/en
Application filed by Glycom AS filed Critical Glycom AS
Publication of WO2005121114A2 publication Critical patent/WO2005121114A2/en
Publication of WO2005121114A3 publication Critical patent/WO2005121114A3/en
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Cosmetics (AREA)

Abstract

The present invention relates to 1,4- and 1,5-anhydro-D-ketoses (monosaccharides, oligosaccharides and various glycoconjugates), e.g. 1,5-anhydro-D-fructose. Moreover, the invention provides synthetic methods and novel intermediates and precursors suitable for their preparation. The methods include catalytic- and/or pyrolitic sulfenic acid elimination of corresponding ß-hydroxy sulfoxides, N-deprotection of N-substituted-aminoglycals, O-deprotection of carbohydrate enolethers and/or O-acyl-substituted carbohydrate enols, and regio- and stereoselective modification and subsequent chemical transformation of bicyclic and/or tricyclic 1,4- and 1,5-anhydro-glycoderivatives. Furthermore, the present invention provides novel applications of 1,4- and 1,5-anhydroketoses within pharmaceutical, food and cosmetic industries.
PCT/DK2005/000377 2004-06-07 2005-06-07 1,5 and 1,4-anhydroketoses, methods for the preparation of 1,5-and 1,4-anhydroketoses, intermediates, and uses of 1,5-and 1,4-anhydroketoses Ceased WO2005121114A2 (en)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
AU2004903036 2004-06-07
AU2004903036A AU2004903036A0 (en) 2004-06-07 Novel 1,5- and 1,4-anhydroketoses
DKPA200401060 2004-07-05
DKPA200401060 2004-07-05
US58856104P 2004-07-16 2004-07-16
US60/588,561 2004-07-16

Publications (2)

Publication Number Publication Date
WO2005121114A2 WO2005121114A2 (en) 2005-12-22
WO2005121114A3 true WO2005121114A3 (en) 2006-10-12

Family

ID=34993323

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/DK2005/000377 Ceased WO2005121114A2 (en) 2004-06-07 2005-06-07 1,5 and 1,4-anhydroketoses, methods for the preparation of 1,5-and 1,4-anhydroketoses, intermediates, and uses of 1,5-and 1,4-anhydroketoses

Country Status (1)

Country Link
WO (1) WO2005121114A2 (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102936268A (en) * 2012-11-13 2013-02-20 江苏吉贝尔药业有限公司 Process for preparing topiramate midbody acetonylidene

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE952814C (en) * 1953-03-10 1956-11-22 Waldhof Zellstoff Fab Process for the preparation of 3, 4, 5-trioxyotetrahydropyran
WO2002026060A1 (en) * 2000-09-27 2002-04-04 Danisco A/S Antimicrobial agent
US20020102342A1 (en) * 1999-03-19 2002-08-01 Andersen Soren Moller 1,5-Anhydro-D-fructose substituted with a hydrophobic group for use as anti-oxidant and/or emulsifier
WO2002089587A1 (en) * 2001-05-08 2002-11-14 Bioprospect Limited Methods and compositions for controlling pests
US20020198158A1 (en) * 2000-01-14 2002-12-26 Bo Ahren Use of a cyclic ether for the preparation of medicaments affecting glucose tolerance

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE952814C (en) * 1953-03-10 1956-11-22 Waldhof Zellstoff Fab Process for the preparation of 3, 4, 5-trioxyotetrahydropyran
US20020102342A1 (en) * 1999-03-19 2002-08-01 Andersen Soren Moller 1,5-Anhydro-D-fructose substituted with a hydrophobic group for use as anti-oxidant and/or emulsifier
US20020198158A1 (en) * 2000-01-14 2002-12-26 Bo Ahren Use of a cyclic ether for the preparation of medicaments affecting glucose tolerance
WO2002026060A1 (en) * 2000-09-27 2002-04-04 Danisco A/S Antimicrobial agent
WO2002089587A1 (en) * 2001-05-08 2002-11-14 Bioprospect Limited Methods and compositions for controlling pests

Non-Patent Citations (6)

* Cited by examiner, † Cited by third party
Title
AIDA, KO: "Oxidative fermentation. XII. Formation of rubiginic acid, a new .gamma.-pyrone derivative, and comenic acid by Gluconoacetobacter liquefaciens", BULLETIN OF THE AGRICULTURAL CHEMICAL SOCIETY OF JAPAN ( 1955 ), 19, 97 -103 CODEN: BACOAV; ISSN: 0375-8397, 1955, XP009065836 *
CROUT, D. H. G. ET AL: "Cardiac glycosides of Calotropis procera", TETRAHEDRON LETTERS 63-7 CODEN: TELEAY; ISSN: 0040-4039, 1963, XP002382637 *
F.W. LICHTENTHALER ET AL.: "A convenient access to 1,5-anhydroketoses", TETRAHEDRON LETTERS, vol. 21, 1980, pages 1429 - 1432, XP002323084 *
NICOLAOU, K. C. ET AL: "Total synthesis of apoptolidin: part 1. Retrosynthetic analysis and construction of building blocks", ANGEWANDTE CHEMIE, INTERNATIONAL EDITION , 40(20), 3849-3854 CODEN: ACIEF5; ISSN: 1433-7851, 2001, XP002382640 *
SHAFIZADEH F ET AL: "1,5-ANHYDRO-4-DEOXY-D-GLYCERO-HEX-1-EN-3-ULOSE AND OTHER PYROLYSIS PRODUCTS OF CELLULOSE", CARBOHYDRATE RESEARCH, AMSTERDAM, NL, vol. 67, no. 2, December 1978 (1978-12-01), pages 433 - 447, XP000925142 *
YOSHINAGA, KAZUHIRO ET AL: "Preparation and reactivity of a novel disaccharide, glucosyl 1,5-anhydro-D-fructose (1,5-anhydro-3-O-.alpha.-glucopyranosyl-D-fructose)", CARBOHYDRATE RESEARCH , 338(21), 2221-2225 CODEN: CRBRAT; ISSN: 0008-6215, 2003, XP002382638 *

Also Published As

Publication number Publication date
WO2005121114A2 (en) 2005-12-22

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