Synthesis of 1,3-di-O-alkyl-2-O-(β-glycosyl)glycerols bearing oligosaccharides as hydrophilic groups

Article abstract of DOI:10.1016/0009-3084(94)90094-9

A novel series of synthetic glycolipids, 1,3-di-O-alkyl-2-O-(β-glycosyl)glycerols, and their efficient synthetic route were proposed.These glyceroglycolipids were synthesized in good overall yields and stereoselectivity in five steps via trichloroacetimidate glycosylation with 1,3-di-O-alkylglycerols.This route was applied to prepare the glycolipids bearing a cello- or malto-oligosaccharide with a definite number of sugar residues from one to six.Thin-layer chromatography, elemental analysis, nuclear magnetic resonance spectroscopy and infrared absorption spectroscopy confirmed that these glycolipids were chemically pure compounds.Keywords: Glyceroglycolipids; Oligosaccharide headgroups; Synthesis