Journal
ORGANIC LETTERS
Volume 11, Issue 20, Pages 4528-4531Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol901723m
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Funding
- Holt Foundation [C2075/ A9106, C2075/A5048]
- MRC [G0601746] Funding Source: UKRI
- Medical Research Council [G0601746] Funding Source: researchfish
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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.
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