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

Fingerprint

Ulcer
Polysaccharides
Disaccharides
Galactose
Ether
Esters
Derivatives
Oxidation
Bupleuran 2IIc
trichloroacetamide
trifluoromethanesulfonic acid
disaccharide receptor

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Organic Chemistry

Cite this

Synthesis of a model compound related to an anti-ulcer pectic polysaccharide. / Maruyama, Michiko; Takeda, Tadahiro; Shimizu, Noriko; Hada, Noriyasu; Yamada, Haruki.

In: Carbohydrate Research, Vol. 325, No. 2, 07.04.2000, p. 83-92.

Research output: Contribution to journalArticle

Maruyama, M, Takeda, T, Shimizu, N, Hada, N & Yamada, H 2000, 'Synthesis of a model compound related to an anti-ulcer pectic polysaccharide', Carbohydrate Research, vol. 325, no. 2, pp. 83-92. https://doi.org/10.1016/S0008-6215(99)00315-8
Maruyama, Michiko ; Takeda, Tadahiro ; Shimizu, Noriko ; Hada, Noriyasu ; Yamada, Haruki. / Synthesis of a model compound related to an anti-ulcer pectic polysaccharide. In: Carbohydrate Research. 2000 ; Vol. 325, No. 2. pp. 83-92.
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