METHOD FOR PRODUCING a-HALO-TETRAACYL-GLUCOSE

摘要

There is provided an efficient and excellent preparation method of an α-halo-tetraacyl-glucose which is suitable for industrial preparation, which comprises reacting D-glucose or lower alkyl D-glucoside with a reactive derivative of a carboxylic acid and a metal halide to prepare the α-halo-tetraacyl-glucose represented by the formula (III):;wherein R represents an optionally substituted lower alkyl group or an optionally substituted aryl group, and X represents a halogen atom,

in one step, and the resulting α-halo-tetraacyl-glucose (III) can be converted into a compound of the formula (I) or a salt thereof by subjecting to a conventional method.

主权项

1. A method for producing an α-halo-tetraacyl-glucose represented by the formula (III): wherein R represents optionally substituted lower alkyl or optionally substituted aryl, and X represents a halogen atom,which comprises reacting D-glucose or lower alkyl D-glucoside with a reactive derivative derived from a carboxylic acid represented by the formula (IV): wherein R represents an optionally substituted lower alkyl or an optionally substituted aryl, (1) in the presence of a metal halide represented by the formula: MX wherein M represents an alkali metal, and X represents a halogen atom, a Lewis acid catalyst and a phase-transfer catalyst; or (2) using an acid halide represented by the formula (V): wherein R represents an optionally substituted lower alkyl or an optionally substituted aryl, and X represents a halogen atomas the reactive derivative derived from the carboxylic acid represented by the formula (IV), in the presence of a catalytic amount of a Lewis acidic metal halide.