Branched-chain sugars. Part X. The synthesis of branched-chain amino-sugars

Abstract

Syntheses are discussed of two types of branched-chain methyl aminoaldopyranosides. Condensation of a methyl glycopyranosidulose with nitromethane followed by reduction of the nitro-group in the product has been examined as a route to branched-chain glycosides in which the branching group carries an amino-residue. To obtain branched-chain aminoglycopyranosides in which the amino-group is attached directly to the pyranoid ring at the site of branching, the base-catalysed cyclisation of periodate-oxidised methyl glycopyranosides with nitroethane or 1-nitropropane and subsequent reduction of the branched-chain C-nitroglycoside has been studied. Examples of both types of modified aminoglycoside are described.