Efficient syntheses of beta-cyanosugars using glycosyl iodides derived from per-O-silylated mono- and disaccharides.
[reaction: see text] Reported herein is a general method for the efficient syntheses of a variety of beta-cyano glycosides through the activation of per-O-trimethylsilyl glycosides with TMSI to form alpha-glycosyl iodides, which undergo S(N)2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH(4) in the presence of catalytic CoCl(2)(H(2)O)(6) in THF/H(2)O to give the corresponding aminomethyl glycosides.
Bhat
A S
AS
Department of Chemistry, The University of Arizona, Tucson, Arizona 85721, USA.
Gervay-Hague
J
J
D004187:Disaccharides / Q000737:chemistry*; D006001:Glycoconjugates / Q000138:chemical synthesis / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D009005:Monosaccharides / Q000737:chemistry*; D009570:Nitriles / Q000737:chemistry*
D004187:Disaccharides; D006001:Glycoconjugates; D006027:Glycosides; D009005:Monosaccharides; D009570:Nitriles