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

共 50 条

[21] AMINO-SUGARS .123. THE SYNTHESIS OF O-BETA-D-MANNOPYRANOSYL-(1-]4)-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]4)-2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE .2.
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[22] SYNTHETIC STUDIES IN CARBOHYDRATES .69. SYNTHESIS OF METHYL O-(2-O-METHYL-BETA-D-GALACTOPYRANOSYL)-(1-]4)-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]3)-BETA-D-GALACTOPYRANOSIDE AND 4-NITROPHENYL O-BETA-D-GALACTOPYRANOSYL-(1-]4)-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]3)-BETA-D-GALACTOPYRANOSIDE
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[23] AN ALTERNATIVE SYNTHESIS OF O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]4)-N-ACETYLNORMURAMOYL-L-ALPHA-AMINOBUTANOYL-D-ISOGLUTAMINE
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[24] SYNTHESES OF 3-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-ALPHA-D-GALACTOPYRANOSE (LACTO-N-BIOSE II) AND 3,4-DI-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-D-GALACTOPYRANOSE
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[26] SYNTHETIC STUDIES IN CARBOHYDRATES .60. SYNTHETIC MUCIN FRAGMENTS - BENZYL O-(2-ACETAMIDO-2-DEOXY-ALPHA-D-GLUCOPYRANOSYL)-(1-]3)-O-BETA-D-GALACTOPYRANOSYL-(1-]3)-O-[(2-ACETAMIDO-I-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]6)]-1-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE AND BENZYL O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]3)-O-BETA-D-GALACTOPYRANOSYL-(1-]3)-O-[BETA-D-GALACTOPYRANOSYL-(1-]6)]-2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDEN
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[28] SYNTHESIS OF ENZYME SUBSTRATES .1. SYNTHESIS OF 6-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-D-MANNOSE
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