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.
Surface Engineering Laboratory, National Institute of Materials and Chemical Research, Ibaraki, Japan.
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H
Minamikawa
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Murakami
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M
Hato
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