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

Authors
Journal
Carbohydrate Research
0008-6215
Publisher
Elsevier
Publication Date
Volume
325
Issue
2
Identifiers
DOI: 10.1016/s0008-6215(99)00315-8
Keywords
  • Acidic Tetrasaccharide
  • Anti-Ulcer Pectic Polysaccharide
  • Bupleurum Falcatum
  • Chemical Synthesis

Abstract

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.

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