Synthesis of a new glycosphingolipid from the marine ascidian Microcosmus sulcatus using a one-pot glycosylation strategy

Isao Ohtsuka, Noriyasu Hada, Toshiyuki Atsumi, Nobuko Kakiuchi

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

A novel neutral glycosphingolipid found in Microcosmus sulcatus containing a β-d-Galp(1→4)[α-d-Fucp-(1→3)]β-d-Glcp-(1→)Cer motif was synthesized. Trisaccharide derivatives were synthesized using trimethylsilyltrifluoromethanesulfanate (TMSOTf) and N-iodosuccimide (NIS)/trifluoromethane sulfonic acid (TfOH) as the promoters. Synthesis was achieved with an efficient one-pot glycosylation strategy. This is the first report of a one-pot glycosylation strategy using the procedure of Boons et al. for the synthesis of a natural product. Coupling of trisaccharide derivative 19 and ceramide derivative 20 by TMSOTf afforded the glycosphingolipid derivative 21. The fully protected glycoside was deprotected to give the target glycosphingolipid 2.

Original languageEnglish
Pages (from-to)1470-1475
Number of pages6
JournalTetrahedron
Volume69
Issue number5
DOIs
Publication statusPublished - 2013 Feb 4

Fingerprint

Glycosylation
Trisaccharides
Urochordata
Glycosphingolipids
Neutral Glycosphingolipids
Derivatives
Sulfonic Acids
Ceramides
Glycosides
Biological Products
fluoroform

Keywords

  • Glycosphingolipids
  • Microcosmus sulcatus
  • Oligosaccharide synthesis
  • One-pot glycosylation strategy

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Synthesis of a new glycosphingolipid from the marine ascidian Microcosmus sulcatus using a one-pot glycosylation strategy. / Ohtsuka, Isao; Hada, Noriyasu; Atsumi, Toshiyuki; Kakiuchi, Nobuko.

In: Tetrahedron, Vol. 69, No. 5, 04.02.2013, p. 1470-1475.

Research output: Contribution to journalArticle

Ohtsuka, Isao ; Hada, Noriyasu ; Atsumi, Toshiyuki ; Kakiuchi, Nobuko. / Synthesis of a new glycosphingolipid from the marine ascidian Microcosmus sulcatus using a one-pot glycosylation strategy. In: Tetrahedron. 2013 ; Vol. 69, No. 5. pp. 1470-1475.
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