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dc.contributor.authorHansen, Steen Uldall
dc.contributor.authorBaráth, Marek
dc.contributor.authorSalameh, Bader A B
dc.contributor.authorPritchard, Robin G
dc.contributor.authorStimpson, William T
dc.contributor.authorGardiner, John M
dc.contributor.authorJayson, Gordon C
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.
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
html.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.


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