Convergent syntheses of C(1→3)-linked disaccharides starting from isolevoglucosenone

被引：30

作者：

Zhu, YH ^{[1
]}

Demange, R ^{[1
]}

Vogel, P ^{[1
]}

机构：

[1] Univ Lausanne, BCH, Chim Sect, CH-1015 Lausanne, Switzerland

来源：

TETRAHEDRON-ASYMMETRY | 2000年 / 11卷 / 01期

关键词：

D O I：

10.1016/S0957-4166(99)00492-9

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Nucleophilic addition (Nu-Mf) to isolevoglucosenone 1 generates enolates stereospecifically (exo face addition) that can be reacted with sugar-derived aldehydes to give C(1-->3)-linked disaccharide precursors with high diastereoselectivity. Limitations of the method arising from unfavorable aldolate stability can be overcome by using Et2AlI as the nucleophile. This leads to products of Baylis-Hillmann condensations. One example is presented and has led to the preparation of 2,3-anhydro-3-C-[(1S)-2,6-anhydro-D-glycero-D-gulo-heptitol-1-C-yl]-beta-D-gulo-pyranose 5. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：263 / 282

页数：20

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