Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Synthetic Studies on Glycosphingolipids from Protostomia Phyla : Synthesis of a Glycosphingolipid Analogue from the Parasite Spirometra erinacei
Noriyasu HADAMayuko KURODATadahiro TAKEDA
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JOURNAL FREE ACCESS

2000 Volume 48 Issue 8 Pages 1160-1165

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Abstract

Novel neutral glycosphingolipids isolated from the plerocercoids of a tapeworm, Spirometra erinacei, may be expected to be involved in host-parasite interactions. We have synthesized this glycosphingolipid analogue containing 2-branched fatty alkyl residue in place of ceramide. Glycosylation of nonreducing-end trisaccharide derivative 15 with the reducing-end disaccharide derivative 17 in the presence of trimethylsilyl triflate (TMSOTf) gave the desired oligosaccharide derivative in good yield. The fully per-O-acylated 2-(trimethylsilyl)ethyl glycoside 19 was converted to glycosylimidate 20, which was condensed with 2-(tetradecyl)hexadecanol and subsequently deacylated to give the target glycosphingolipid analogue 22.

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© The Pharmaceutical Society of Japan
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