New method for the synthesis of 6-amino-6-deoxy-α-D-glucopyranosides

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Abstract
A general method for the synthesis of 6-amino-6-deoxy-α-D-glucopyranosides from 3,4-di-O-acetyl-1,2-dideoxy-6-O-p-tolylsulfonyl-D-arabino-hex-1-enopyranose (3,4-di-O-acetyl-6-O-p-tolylsulfonyl-D-glucal) is described. The key steps in the synthesis are addition of nitrosyl chloride to the above glycal, condensation of the resulting nitroso–chloro adduct with alcohols or phenols to provide α-glycosides of 3,4-di-O-acetyl-2-oximino-6-O-p-tolylsulfonyl-D-arabino-hexopyranose, and conversion of the α-oximino-glycosides to α-glucoside derivatives. Propyl, isopropyl, phenyl, and L-menthyl 2,3,4-tri-O-acetyl-6-O-p-tolylsulfonyl-α-D-glucopyranosides are thus prepared and the last compound is converted to L-menthyl 6-amino-6-deoxy-α-D-glucopyranoside.

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