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

研究成果: Article査読

7 被引用数 (Scopus)

抄録

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.

本文言語English
ページ(範囲)1470-1475
ページ数6
ジャーナルTetrahedron
69
5
DOI
出版ステータスPublished - 2013 2 4

ASJC Scopus subject areas

  • 生化学
  • 創薬
  • 有機化学

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