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Efficient chemoenzymatic enantioselective synthesis of diacylglycerols (DAG)

2004; Elsevier BV; Volume: 15; Issue: 18 Linguagem: Inglês

10.1016/j.tetasy.2004.07.040

1362-511X

Giuseppe Guanti, Luca Banfi, Andrea Basso, E. M. Bevilacqua, Laura Bondanza, Renata Riva,

Glycosylation and Glycoproteins Research

A new efficient chemoenzymatic methodology for the production of 3-O-benzyl-sn-glycerol and 1,2-O-dipalmitoyl-sn-glycerol has been developed. It starts from racemic 1-O-benzylglycerol and is based on the sequential enzymatic acylation––Mitsunobu inversion––enzymatic hydrolysis, which has been performed without isolation of the intermediates. In this way a 70–75% yield of 3-O-benzyl-sn-glycerol with 94–96% ee has been obtained.