Addition of trialkylaluminum reagents to glyconolactones.: Synthesis of 1-C-methyl GlcNAc oxazoline and thiazoline

被引：13

作者：

Knapp, S ^{[1
]}

Yang, CH ^{[1
]}

Haimowitz, T ^{[1
]}

机构：

[1] Rutgers State Univ, Dept Chem & Biol Chem, Piscataway, NJ 08854 USA

来源：

TETRAHEDRON LETTERS | 2002年 / 43卷 / 39期

关键词：

D O I：

10.1016/S0040-4039(02)01506-X

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Addition of carbon nucleophiles to 2-acetamido-2-deoxygluconolactones fails for many reagents, but trialkylaluminums add alkyl smoothly. The product of Methyl addition to 2-acetamido-2-deoxy-D-gluconolactone has been converted to 1-C-methyl GlcNAc thiazoline, a potential N-acetylhexosaminidase inhibitor, and to an O-protected I-C-Me GlcNAc oxazoline, a potential I-C-Me GlcNAc donor. (C) 2002 Elsevier Science Ltd. All rights reserved.

引用

页码：7101 / 7104

页数：4

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