Synthetic studies on glycosphingolipids from protostomia phyla: Synthesis of a glycosphingolipid analogue from the parasite Spirometra erinacei

N. Hada, M. Kuroda, T. Takeda

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20 Citations (Scopus)

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 nonreducingo-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.

Original languageEnglish
Pages (from-to)1160-1165
Number of pages6
JournalChemical and Pharmaceutical Bulletin
Volume48
Issue number8
DOIs
Publication statusPublished - 2000 Jan 1

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Keywords

  • Chemical synthesis
  • Glycosphingolipid
  • Glycosylation
  • Spirometra erinacei

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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