Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-O-silylated Mono- and Disaccharides

Reported herein is a general method for the efficient syntheses of a variety of β-cyano glycosides through the activation of per-O-trimethylsilyl glycosides with TMSI to form α-glycosyl iodides, which undergo SN2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides wer...

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Bibliographic Details
Published in:Organic letters 2001-06, Vol.3 (13), p.2081-2084
Main Authors: Bhat, Abhijit S, Gervay-Hague, Jacquelyn
Format: Article
Language:English
Subjects:
Disaccharides - chemistry
Glycoconjugates - chemical synthesis
Glycoconjugates - chemistry
Glycosides - chemical synthesis
Glycosides - chemistry
Monosaccharides - chemistry
Nitriles - chemistry
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Summary:Reported herein is a general method for the efficient syntheses of a variety of β-cyano glycosides through the activation of per-O-trimethylsilyl glycosides with TMSI to form α-glycosyl iodides, which undergo SN2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)6 in THF/H2O to give the corresponding aminomethyl glycosides.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0160405