Scalable synthesis of L-iduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides.

2.50
Hdl Handle:
http://hdl.handle.net/10541/109286
Title:
Scalable synthesis of L-iduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides.
Authors:
Hansen, Steen Uldall; Baráth, Marek; Salameh, Bader A B; Pritchard, Robin G; Stimpson, William T; Gardiner, John M; Jayson, Gordon C ( 0000-0002-8515-8944 )
Abstract:
L-ido cyanohydrin 3 was prepared from diacetone-D-glucose in four steps and 76% overall yield and 90% de via cyanohydrin reaction of aldehyde 2. This process can be scaled to provide >1 mol of pure L-ido cyanohydrin 3. Cyanohydrin 3 was elaborated to 1,2-isopropylidine-protected L-ido nitrile (8), iduronic amide 9, and known carboxy ester 10. Coupling of 8 and 9 with glucosamine donors leads to new types (6-cyano and 6-carboxamide) of heparin-related disaccharides.
Affiliation:
School of Chemistry and Manchester Interdisciplinary Biocentre, The University of Manchester, 131 Princess Street, Manchester M1 7DN, UK. gardiner@manchester.ac.uk
Citation:
Scalable synthesis of L-iduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides. 2009, 11 (20):4528-31 Org. Lett.
Journal:
Organic Letters
Issue Date:
15-Oct-2009
URI:
http://hdl.handle.net/10541/109286
DOI:
10.1021/ol901723m
PubMed ID:
19764712
Type:
Article
Language:
en
ISSN:
1523-7052
Appears in Collections:
All Christie Publications ; Medical Oncology

Full metadata record

DC FieldValue Language
dc.contributor.authorHansen, Steen Uldallen
dc.contributor.authorBaráth, Mareken
dc.contributor.authorSalameh, Bader A Ben
dc.contributor.authorPritchard, Robin Gen
dc.contributor.authorStimpson, William Ten
dc.contributor.authorGardiner, John Men
dc.contributor.authorJayson, Gordon Cen
dc.date.accessioned2010-08-09T12:34:06Z-
dc.date.available2010-08-09T12:34:06Z-
dc.date.issued2009-10-15-
dc.identifier.citationScalable synthesis of L-iduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides. 2009, 11 (20):4528-31 Org. Lett.en
dc.identifier.issn1523-7052-
dc.identifier.pmid19764712-
dc.identifier.doi10.1021/ol901723m-
dc.identifier.urihttp://hdl.handle.net/10541/109286-
dc.description.abstractL-ido cyanohydrin 3 was prepared from diacetone-D-glucose in four steps and 76% overall yield and 90% de via cyanohydrin reaction of aldehyde 2. This process can be scaled to provide >1 mol of pure L-ido cyanohydrin 3. Cyanohydrin 3 was elaborated to 1,2-isopropylidine-protected L-ido nitrile (8), iduronic amide 9, and known carboxy ester 10. Coupling of 8 and 9 with glucosamine donors leads to new types (6-cyano and 6-carboxamide) of heparin-related disaccharides.en
dc.language.isoenen
dc.subject.meshAir-
dc.subject.meshDisaccharides-
dc.subject.meshHeparin-
dc.subject.meshIduronic Acid-
dc.subject.meshIndicators and Reagents-
dc.subject.meshNitriles-
dc.subject.meshStereoisomerism-
dc.subject.meshSubstrate Specificity-
dc.subject.meshTemperature-
dc.titleScalable synthesis of L-iduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides.en
dc.typeArticleen
dc.contributor.departmentSchool of Chemistry and Manchester Interdisciplinary Biocentre, The University of Manchester, 131 Princess Street, Manchester M1 7DN, UK. gardiner@manchester.ac.uken
dc.identifier.journalOrganic Lettersen

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