Solvent-free synthesis of 1,2:5,6-di-O-isopropylidene-3-O-3' -(N',N'-dimethylamino-n-propyl)-alpha,D-glucofuranose and 1,2:5,6-di-O-isopropylidene-3-O-heptyl-alpha,D-glucofuranose.

摘要

A solvent-free method for synthesizing an ethereally-substituted, blocked monosaccharide comprising the steps of: 1) mixing, in the absence of solvent, a partially blocked monosaccharide unblocked at one position, an alkyl halide or a substituted alkyl halide, and an anhydrous alkali base; 2) heating the mixture to a temperature sufficient to allow the mixture to react; 3) maintaining the mixture at a suitable temperature for a time sufficient to form an ethereally-substituted blocked monosaccharide and drive off any water produced; 4) removing any unreacted alkyl halide or substituted alkyl halide from the mixture; 5) recovering the ethereally-substituted blocked monosaccharide product from the mixture; and, optionally, 6) selectively hydrolyzing the ethereally-substituted blocked monosaccharide product to remove one or more of the acetal blocking groups. e