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

被引：24

作者：

Maruyama, M

Takeda, T

Shimizu, N

Hada, N

Yamada, H

机构：

[1] Kyoritsu Coll Pharm, Minato Ku, Tokyo 1058512, Japan

[2] Kitasato Inst, Oriental Med Res Ctr, Minato Ku, Tokyo 1088642, Japan

来源：

CARBOHYDRATE RESEARCH | 2000年 / 325卷 / 02期

关键词：

acidic tetrasaccharide; anti-ulcer pectic polysaccharide; Bupleurum falcatum; chemical synthesis;

D O I：

10.1016/S0008-6215(99)00315-8

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

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. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：83 / 92

页数：10

共 14 条

[1] SELECTIVE OXIDATION OF MONOSACCHARIDE DERIVATIVES TO URONIC-ACIDS [J].