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

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)-alpha-L-rhamnopyranosyl-(1-- >4)-2,3,6-tri-O-benzyl-alpha-D-galactopyranosyl trichloroacetimidate, with the disaccharide receptor, allyl 3,4-di-O-benzyl-alpha-L-rhamnopyranosyl-(1-->4)-2,3,6-tri-O-benzyl-beta- 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 alpha-L-Rha-(1-->4)-alpha-D-GalA-(1-->2)-alpha-L-Rha-(1-->4)-beta-D-GalA , via removal of the corresponding ether and ester protecting groups, followed by oxidation.

• Authors: M Maruyama, T Takeda, N Shimizu, N Hada, H Yamada
• Journal: Carbohydrate research (Carbohydr Res) Vol. 325 Issue 2 Pg. 83-92 (Apr 07 2000) ISSN: 0008-6215 [Print] Netherlands
• PMID: 10795816 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Anti-Ulcer Agents
• Bupleuran 2IIc
• Pectins

Topics

• Anti-Ulcer Agents (chemical synthesis, chemistry)
• Carbohydrate Sequence
• Magnetic Resonance Spectroscopy
• Models, Chemical
• Molecular Sequence Data
• Pectins (chemical synthesis, chemistry)