Synthesis of a model compound related to an anti-ulcer pectic polysaccharide

Michiko Maruyama, Tadahiro Takeda, Noriko Shimizu, Noriyasu Hada, Haruki Yamada

Research output: Contribution to journalArticle

28 Citations (Scopus)

Abstract

A stereocontrolled synthesis of the model compound for an anti-ulcer active polysaccharide (Bupleuran 2IIc) is described. Glycosidation of the disaccharide acceptor, 2-O-acetyl-3-O-benzyl-4-O-(p-methoxybenzyl)-α-L-rhamnopyranosyl-(1→4)-2,3,6-tri-O-benzyl-α-D-galactopyranosyl trichloroacetimidate, with the disaccharide receptor, allyl 3,4-di-O-benzyl-α-L-rhamnopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-galactopyranoside, using silver triflate (AgOTf) as a promoter gave the desired tetrasaccharide derivative, which was transformed into the acidic tetrasaccharide, corresponding to a segment of the rhamnogalacturonan (Bupleuran 2IIc) polysaccharide, propyl α-L-Rha-(1→4)-α-D-GalA-(1→2)-α-L-Rha-(1→4)-β-D-GalA, via removal of the corresponding ether and ester protecting groups, followed by oxidation. Copyright (C) 2000 Elsevier Science Ltd.

Original languageEnglish
Pages (from-to)83-92
Number of pages10
JournalCarbohydrate Research
Volume325
Issue number2
DOIs
Publication statusPublished - 2000 Apr 7

Keywords

  • Acidic tetrasaccharide
  • Anti-ulcer pectic polysaccharide
  • Bupleurum falcatum
  • Chemical synthesis

ASJC Scopus subject areas

  • Analytical Chemistry
  • Biochemistry
  • Organic Chemistry

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