CYANOSUGARS III. THE REACTION OF TRIMETHYLSILYL CYANIDE WITH KETO, EPOXY AND ACETAL DERIVATIVES OF CARBOHYDRATES.

Article abstract of DOI:10.1016/S0040-4020(01)91407-3

Reaction of methyl 2-acetamido-4,6-O-benzylidene-2-deoxy-α-D-ribohexopyranosid-3-ulose with Me3SiCN afforded methyl 2-acetamido-4,6-O-benzylidene-3-C-cyano-2-deoxy-3-O-trimethylsilyl-α-D-allo-hexopyranoside.Reaction of ethyl 4,6-di-O-acetyl-2,3-anhydro-α-D-mannopyranoside with Me3SiCN gave the corresponding ethyl 4,6-di-O-acetyl-2-C-cyano-2-deoxy-α-D-glucopyranoside.Reaction of methyl 4,6-O-benzylidene 2,3-anhydro-α-D-allopyranoside or methyl 4,6-O-benzylidene-2,3-di-O-tosyl-α-D-glucopyranoside with Me3SiCN at -75 deg C or -50 deg C gave the corresponding methyl 6-O-<(R)-cyano phenyl methyl>-α-D-glucopyranosides with high or total regio and stereoselectivity.