Synthesis of some partially methylated sucrose derivatives

Abstract

1',6,6'-Tri-O-methylsucrose, a new compound, has been synthesized by methylation of 2,3,3',4,4'-penta-O-acetylsucrose with diazomethane and boron trifluoride with subsequent deacetylation. 2,3,3',4,4'-Penta-O-methylsucrose has been obtained in improved yield from the tri-O-trityl derivative by reduction with lithium in liquid ammonia. A major product of the incomplete methylation of 11,6,6'-tri-O-tritylsucrose was the 2,3,3',4'-tetra-O-methyl derivative, and after reductive detritylation 2,3,3',4'-tetra-O-methylsucrose, a new compound, was isolated and identified by examination of its hydrolysis products.