Scalable synthesis of L-iduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides.
Authors
Hansen, Steen UldallBaráth, Marek
Salameh, Bader A B
Pritchard, Robin G
Stimpson, William T
Gardiner, John M
Jayson, Gordon C
Affiliation
School of Chemistry and Manchester Interdisciplinary Biocentre, The University of Manchester, 131 Princess Street, Manchester M1 7DN, UK. gardiner@manchester.ac.ukIssue Date
2009-10-15
Metadata
Show full item recordAbstract
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.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 LettersDOI
10.1021/ol901723mPubMed ID
19764712Type
ArticleLanguage
enISSN
1523-7052ae974a485f413a2113503eed53cd6c53
10.1021/ol901723m
Scopus Count
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