EFFICIENT SYNTHESIS OF O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-SER/THR BUILDING-BLOCKS FOR SPPS OF O-GLCNAC GLYCOPEPTIDES

被引：24

作者：

MEINJOHANNS, E ^{[1
]}

MELDAL, M ^{[1
]}

BOCK, K ^{[1
]}

机构：

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

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 50期

关键词：

D O I：

10.1016/0040-4039(95)01941-A

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Suitably protected building blocks for solid-phase synthesis of beta-O-GlcNAc glycopeptides. N-alpha-Fmor-Ser(Ac-3-beta-D-GlcNAc)-OPfp 10 and N-alpha-Fmoc-Thr(AL(3)-beta-D-GlcNAc)-OPfp 11 have been synthesized by stereoselective glycosylation of N-alpha-Fmoc-Ser-OPfE 6 and N-alpha-Fmoc-Thr-OPfp 7, respectively. with the 2-trichloroethoxycarbonylamino (Teoc) glycosyl donors 3 and 5, followed by in situ reduction of the Teoc-group and simultaneous N-acetylation using zinc dust in tetrahydrofuranlacetic anhydridelacetic acid (3:2:1).

引用

页码：9205 / 9208

页数：4

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