Scalable synthesis of L-iduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides.
Hansen, Steen Uldall Baráth, Marek Salameh, Bader A B Pritchard, Robin G Stimpson, William T Gardiner, John M Jayson, Gordon C
Hansen, Steen Uldall
Baráth, Marek
Salameh, Bader A B
Pritchard, Robin G
Stimpson, William T
Gardiner, John M
Jayson, Gordon C
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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.
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2009-10-15
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Article
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Scalable synthesis of L-iduronic acid derivatives via stereocontrolled cyanohydrin reaction for synthesis of heparin-related disaccharides. 2009, 11 (20):4528-31 Org. Lett.