Synthesis of glycoglycerolipid of 1,2-dipalmitoyl-3-(N-palmitoyl-6′-amino-6′-deoxy-α-d-glucosyl)-sn-glycerol and its analogues, inhibitors of human Myt1-kinase

Abstract

A glycoglycerolipid 1a isolated from a marine alga showed inhibition to Myt1 kinase with IC(50) of 0.12 μg/mL. We synthesized 1a and its seven analogues (1b-h) in an efficient method with high stereoselectivity. The process employed trichloroacetimidate donor 4b at low substrate concentration to achieve high α-selectivity (α/β=33:1) in glycosylation reaction. The present synthesis provided various acyl derivatives required for the study on the structure-activity relationship later.