ChemInform Abstract: Diastereoselective Addition of Amines to Vinyl Sulfone Modified Carbohydrates: A Highly Flexible Methodology for the Synthesis of New Classes of Deoxyaminosugars.

Methyl 2,3 -dideoxy-4, 6-O-(phenylmethylene)-3-C-phenylsulfonyl-alpha-D -erythro -hex-2-enopyranoside (5 alpha) and methyl 2,3-dideoxy-4,6-0-(phenylmethylene)-3-C-pyranoside (5 beta) have been subjected to Michael addition reaction with various amines to develop a new methodology for the synthesis of new classes of aminosugars. Compound 5a reacted with primary amines to generate gluco- derivatives, but secondary amines produced both gluco- (major) and manno- (minor) isomers. Compound 5 beta, on the other hand, produced only gluco- isomers with both primary and secondary amines. The stereochemical course of addition of some of the amines to 5 alpha and 5 beta are significantly different from that of the addition of amines to 3-nitroenopyranoses. The present route to the syntheses of various aminosugars with gluco- configurations from 5 alpha and 5 beta constitutes a novel method for the introduction of N-monoalkylated and N,N-dialkylated amines to the C-2 carbon of pyranoses in equatorial configurations.