Facile syntheses of the trisaccharide acceptors - The key intermediates for assembling the elicitor hexasaccharide

被引：6

作者：

Wang, W ^{[1
]}

Kong, FZ ^{[1
]}

机构：

[1] Acad Sinica, Res Ctr Ecoenvironm Sci, Beijing 100085, Peoples R China

来源：

SYNTHETIC COMMUNICATIONS | 1999年 / 29卷 / 18期

基金：

中国国家自然科学基金;

关键词：

D O I：

10.1080/00397919908085942

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile synthesis of trisaccharide 7, the key intermediate for assembling phytoalexin glucohexatose elicitor, was achieved via orthoester formation-rearrangement from stepwise coupling of 1,2-O-ethylidene-alpha-D-glucopyranose (2) with 2, 3,4-tri-O-acetyl-6-O-chloroacetyl-alpha-D-glucopyranosyl bromide at 6-position and with acetobromoglucose at 3-position respectively. Similar strategy was used for the synthesis of 14.

引用

页码：3179 / 3190

页数：12

共 18 条

[1]

ALDINGTON S, 1992, ADV BOT RES, V19, P1

[2] SYNTHESES OF A HEPTASACCHARIDE BETA-LINKED TO AN 8-METHOXYCARBONYL-OCT-1-YL LINKING ARM AND OF A DECASACCHARIDE WITH STRUCTURES CORRESPONDING TO THE PHYTOELICITOR ACTIVE GLUCAN OF PHYTOPHTHORA-MEGASPERMA F-SP GLYCINEA [J].

BIRBERG, W ;

FUGEDI, P ;

GAREGG, PJ ;

PILOTTI, A .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1989, 8 (01) :47-57

[3] Azido-phenylselenylation of 3-O-benzyl-2-deoxy-5,6-O-isopropylidene-D-arabino-1,4-anhydro-hex-1-enitol: Convenient preparation of 2-azido-2-deoxy-D-glucofurano- and glucopyranoside donors. [J].

Chelain, E ;

Czernecki, S ;

Chmielewski, M ;

Kaluza, Z .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1996, 15 (05) :571-579

[4] A SPECIFIC, HIGH-AFFINITY BINDING-SITE FOR THE HEPTA-BETA-GLUCOSIDE ELICITOR EXISTS IN SOYBEAN MEMBRANES [J].

CHEONG, JJ ;

HAHN, MG .

PLANT CELL, 1991, 3 (02) :137-147

[5]

FLETCHER HG, 1963, METHODS CARBOHYDRATE, V2, P231

[6] SYNTHESES OF A BRANCHED HEPTASACCHARIDE HAVING PHYTO-ALEXIN-ELICITOR ACTIVITY [J].

FUGEDI, P ;

BIRBERG, W ;

GAREGG, PJ ;

PILOTTI, A .

CARBOHYDRATE RESEARCH, 1987, 164 :297-312

[7] SYNTHESIS OF A HEPTASACCHARIDE, STRUCTURALLY RELATED TO THE PHYTOELICITOR ACTIVE GLUCAN OF PHYTOPHTHORA-MEGASPERMA F-SP GLYCINEA [J].

FUGEDI, P ;

GAREGG, PJ ;

KVARNSTROM, I ;

SVANSSON, L .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1988, 7 (02) :389-397

[8]

HONG N, 1990, TETRAHEDRON LETT, V31, P3179

[9]

HONG N, 1993, P JPN ACAD, V698, P55

[10] SYNTHESIS OF AN ELICITOR-ACTIVE HEPTAGLUCAN SACCHARIDE FOR INVESTIGATION OF DEFENSE-MECHANISMS OF PLANTS [J].

LORENTZEN, JP ;

HELPAP, B ;

LOCKHOFF, O .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (12) :1681-1682

← 1 2 →