On the use of organotin reagents for the preparation of partially esterified glycerol and meso-erythritol

Abstract

The use of dibutylstannylene ketals of two polyhydric alcohols is explored with the aim at the regiospecific preparation of partially esterified glycerol and meso-erythritol. The mono-dibutylstannylene ketal of glycerol with palmitoyl chloride gave both 1,3-diglyceride and 1-monoglyceride. The mono- and the bis-dibutylstannylene ketals of meso-erythritol with palmitoyl chloride under 1 : 1 and 1 : 2 mole ratios, respectively, gave the same product, 1,2,4-tripalmitoyl-meso-erythritol, while the bis-dibutylstannylene ketal of meso-erythritol and palmitoyl chloride (1 : 1 mole ratio) gave tri- and di-esters of meso-erythritol. The probable paths to these products are discussed.