Synthesis of 6'-acylamido-6'-deoxy-α-D-galactoglycerolipids

Abstract

Aminoglycoglycerolipid 1a isolated from an algal extract showed activity against the enzyme Myt1 kinase with an IC50 value of 0.12 μg/mL. Its analogues, 6'-acylamido-6'-deoxy-α-D-galactoglycerolipids (2a-g) were synthesized in an efficient way with high stereoselectivity. The key step was to employ a 4-OAc protecting group of the galactosyl donor 14 as a remote neighboring participation group to give the glycoside with high α-anomeric selectivity (α:β=32:1) in the glycosylation. The preliminary bioactivity screening showed that compound 2g exhibited good inhibition against Myt1 kinase.