GLYCOSYLATION OF PHENOLS - PREPARATION OF 1,2-CIS AND 1,2-TRANS GLYCOSYLATED TYROSINE DERIVATIVES TO BE USED IN SOLID-PHASE GLYCOPEPTIDE SYNTHESIS

被引：54

作者：

JENSEN, KJ ^{[1
]}

MELDAL, M ^{[1
]}

BOCK, K ^{[1
]}

机构：

[1] CARLSBERG LAB, DEPT CHEM, GAMLE CARLSBERG VEJ 10, DK-2500 VALBY, DENMARK

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1993年 / 17期

关键词：

D O I：

10.1039/p19930002119

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The synthesis of four building blocks, N(alpha)-Fmoc-Tyr(Ac4-beta-D-Glc)-OPfp 6, N(alpha)-Fmoc-Tyr(Bz4-alpha-D-Glc)-OPfp 16, N(alpha)-Fmoc-Tyr[Ac4-alpha-D-Glc-(1-->4)-Ac3-beta-D-Glc]-OPfp 9 and N(alpha)-Fmoc-Tyr[Bz4-alpha-D-Glc-(1-->4)-Bz3-alpha-D-Glc]-OPfp 19, suitable for solid-phase glycopeptide synthesis is described. Several different glycosylation procedures were evaluated for this purpose. A remarkable solvent effect on the alpha:beta ratio was observed on going from dichloromethane to the nucleophilic solvent acetonitrile for the glycosylation reactions promoted by silver triflate with participating protecting groups in the 2-position of the glycosyl donor.

引用

页码：2119 / 2129

页数：11

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