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

2001-05-25T00:00:00Z (GMT) by Abhijit S. Bhat Jacquelyn Gervay-Hague
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.