A Facile Stereoselective Synthesis of Ether-Linked β-D-Maltosyl- and β-D-Lactosyl-glycerolipids via Peracetylated Disaccharide α-Phosphoramidates

Abstract

The reaction of 1-O-hexadecyl-2-O-methyl-sn-glycerol with 2,3,6,2′,3′,4′,6′-hepta-O-acetyl-α-lactosylphosphoramidate or α-maltosylphos-phoramidate in the presence of trimethylsilyl triflate and molecular sieves afforded 1-O-hexadecyl-2-O-methyl-3-O-(2,3,6,2′,3′,4′,6′-hepta-O-acetyl-β-lactosyl)-sn-glycerolipid or β-maltosyl-sn-glycerolipid stereoselectively in moderate yields after column chromatography. Alkaline hydrolysis of the O-peracetyl glycerolipids gave the desired β-glycolipids 1 and 2.