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Start Over Author "Baráth, Marek" Publisher american chemical society
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3. Scalable synthesis of L-iduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides.

Author

Hansen SU, Baráth M, Salameh BA, Pritchard RG, Stimpson WT, Gardiner JM, and Jayson GC

Subjects
Air, Indicators and Reagents chemistry, Stereoisomerism, Substrate Specificity, Temperature, Disaccharides chemical synthesis, Disaccharides chemistry, Heparin chemistry, Iduronic Acid analogs & derivatives, Iduronic Acid chemical synthesis, Nitriles chemistry
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.

Published
2009
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