Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-<i>O</i>-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-<i>O</i>-trimethylsilyl glycosides with TMSI to form α-glycosyl iodides, which undergo S<sub>N</sub>2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH<sub>4</sub> in the presence of catalytic CoCl<sub>2</sub>(H<sub>2</sub>O)<sub>6</sub> in THF/H<sub>2</sub>O to give the corresponding aminomethyl glycosides.