SYNTHETIC STUDIES ON PLANT CELL-WALL GLYCANS .6. SYNTHESIS OF (1-]4)-LINKED GALACTURONIC ACID TRISACCHARIDES, A PROPOSED PLANT WOUND-HORMONE AND A STEREOISOMER

被引：21

作者：

NAKAHARA, Y

OGAWA, T

机构：

[1] RIKEN (The Institute of Physical and Chemical Research), Wako-shi, Saitama

来源：

CARBOHYDRATE RESEARCH | 1990年 / 200卷

关键词：

D O I：

10.1016/0008-6215(90)84203-7

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：

Syntheses of α-GalA-(1→4)-α-GalA-(1→4)-GalA, a proposed plant wound-hormone, and its stereoisomer β-GalA-(1→4)-α-GalA-(1→4)-GalA are described. The key intermediates, tert-butyldiphenylsilyl O-(6-O-acetyl-2,3,4-tri-O-benzyl-α-d-galactopyranosyl)-(1→4)-O-(6-O-acetyl-2,3-di-O-benzyl-α-d-galacto- pyranosyl)-(1→4)-6-O-acetyl-2,3-di-O-benzyl-β-d-galactopyranoside and tert-butyldiphenylsilyl O-(6-O- acetyl-2,3,4-tri-O-benzyl-β-d-galactopyranosyl)-(1→4)-O-(6-O-acetyl-2,3-di-O-benzyl-α-d-galactopyranosyl)-(1→4)- 6-O-acetyl-2,3-di-O-benzyl-β-d-galactopyranoside, were prepared by stereoselective α-glycosylation of tert-butyldiphenylsilyl 6-O-acetyl-2,3-di-O-benzyl-β-d-galactopyranoside with O-(6-O-acetyl-2,3, 4-tri-O-benzyl-α-d-galactoyranosyl)-(1→4)-6-O-acetyl-2,3-di-O-benzyl-d-galactopyranosyl fluoride and O-(6-O-acetyl-2,3,4-tri-O-benzyl-β-d-galactopyranosyl)-(1→4)-6-O-acetyl-2,3-di-O-benzyl-d-galactopyranosyl fluoride, respectively. The corresponding β isomers were minor products. Characteristic features in the n.m.r. data of the key intermediates are discussed. © 1990.

引用

页码：363 / 375

页数：13

共 30 条

[1] TRIFLUOROMETHYL SULFATES OF TIN [J].