Synthesis of glycosyl glycerols and related glycolipids

Article abstract of DOI:10.1080/07328309808007465

Several isomeric glycosyl glycerols were synthesized. Acetylated allyl glycosides of D-glucose and D-galactose were transformed into 1-O-(glycopyranosyl)-rac-glycerols in a three step procedure via the corresponding 2,3-epoxypropyl glycosides and the peracetylated glycosyl glycerols. Tetra-O-benzyl-D-glucose was glycosylated with 1,3-di-O-benzylglycerol to give the α-anomer preferentially. The 2-O-(tetra-O-acetyl-β-glycopyranosyl)-sn-glycerols and 2-O-(β-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding α-derivatives of D-mannose were synthesized by selective glycosylation methods from 1,3-di-O-benzylglycerol and 1,3-O-benzylideneglycerol, respectively, and activated sugar compounds followed by hydrogenolysis. After long chain acylation and selective deacetylation the 1,3-di-O-acyl-2-O-β-glycopyranosyl)-sn-glycerols of D-glucose, D-galactose and N-acetyl-D-glucosamine and the corresponding α-derivative of D-mannose were synthesized.

Full text of DOI:10.1080/07328309808007465

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Journal of Carbohydrate Chemistry
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Synthesis of Glycosyl Glycerols and
Related Glycolipids
René Suhr a , Oliver Scheel b & Joachim Thiem a
a Institute of Organic Chemistry, University of Hamburg, Martin-
Luther-King-Platz 6, D-20146, Hamburg, Germany
b Beiersdorf AG, Unnastr 48, D-20253, Hamburg, Germany
Version of record first published: 18 Aug 2006.
To cite this article: René Suhr, Oliver Scheel & Joachim Thiem (1998): Synthesis of Glycosyl Glycerols
and Related Glycolipids, Journal of Carbohydrate Chemistry, 17:6, 937-968
To link to this article: http://dx.doi.org/10.1080/07328309808007465
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