102219-85-2Relevant academic research and scientific papers
CYANOSUGARS III. THE REACTION OF TRIMETHYLSILYL CYANIDE WITH KETO, EPOXY AND ACETAL DERIVATIVES OF CARBOHYDRATES.
Heras, Federico G. De las,San Felix, Ana,Calvo-Mateo, Ana,Fernandez-Resa, Piedad
, p. 3867 - 3874 (2007/10/02)
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--α-D-glucopyranosides with high or total regio and stereoselectivity.
