Synthesis of 1,3-di-O-alkyl-2-O-(beta-glycosyl)glycerols bearing oligosaccharides as hydrophilic groups.
A novel series of synthetic glycolipids, 1,3-di-O-alkyl-2-O-(beta-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.
Minamikawa
H
H
Surface Engineering Laboratory, National Institute of Materials and Chemical Research, Ibaraki, Japan.
Murakami
T
T
Hato
M
M
D002240:Carbohydrate Sequence; D002855:Chromatography, Thin Layer; D006017:Glycolipids / Q000032:analysis / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000737:chemistry*; D013055:Spectrophotometry, Infrared; D013402:Sugar Alcohols / Q000138:chemical synthesis* / Q000737:chemistry
D006017:Glycolipids; D009844:Oligosaccharides; D013402:Sugar Alcohols