Synthesis of di-branched heptasaccharide by one-pot glycosylation using seven independent building blocks

被引：75

作者：

Tanaka, H ^{[1
]}

Adachi, M ^{[1
]}

Tsukamoto, H ^{[1
]}

Ikeda, T ^{[1
]}

Yamada, H ^{[1
]}

Takahashi, T ^{[1
]}

机构：

[1] Tokyo Inst Technol, Dept Appl Chem, Grad Sch Sci & Engn, Tokyo 1528552, Japan

来源：

ORGANIC LETTERS | 2002年 / 4卷 / 24期

关键词：

D O I：

10.1021/ol020150+

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe an efficient synthesis of di-branched heptasaccharide 1 having phytoalexin elicitor activity in soybeans by one-pot glycosylation. The synthesis involves chemo- and regioselective sequential six-step glycosylations using seven independent building blocks and sequential removal of acyl- and benzyl ether-type protecting groups. The coupling of seven building blocks requires only four chemoselective activitable leaving groups of glycosyl donors. Both the glycosylation and deprotection reactions can be achieved utilizing a parallel manual synthesizer.

引用

页码：4213 / 4216

页数：4

共 72 条

[21]

GRICE P, 1995, SYNLETT, P781

[22]

GRINCE P, 1997, CHEM-EUR J, V3, P431

[23]

HONG N, 1990, TETRAHEDRON LETT, V31, P3179

[24] STEREOCONTROLLED INTRODUCTION OF DEUTERIUM ATOMS INTO A PHYTOALEXIN ELICITOR-ACTIVE BETA-D-GLUCOHEXAOSIDE [J].