C-Arylglucoside synthesis:: triisopropylsilane as a selective reagent for the reduction of an anomeric C-phenyl ketal

被引：42

作者：

Ellsworth, BA

Doyle, AG

Patel, M

Caceres-Cortes, J

Meng, W

Deshpande, PP

Pullockaran, A

Washburn, WN

机构：

[1] Bristol Myers Squibb Co, Dept Metab Dis Discovery Chem, Princeton, NJ 08543 USA

[2] Bristol Myers Squibb Co, Dept Preclin Candidate Optimizat, Princeton, NJ 08543 USA

[3] Bristol Myers Squibb Co, Dept Proc Res & Dev, Princeton, NJ 08543 USA

来源：

TETRAHEDRON-ASYMMETRY | 2003年 / 14卷 / 20期

关键词：

D O I：

10.1016/j.tetasy.2003.08.007

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

Reduction of tetra-O-benzyl-protected 1C-phenylglucoside using triethylsilane and (BF3OEt2)-O-. has been reported (Czernecki. S.: Ville. G. J. Org. Chem. 1989, 54, 610-612) to give exclusively 2,3,4,6-tetra-a-O-benzyl-beta-1C-phenyl-1-deoxyglucoside. We have determined that this reduction actually gives a 4:1 mixture of anomers (beta:alpha). We observed that the selectivity of the reduction is influenced by the steric bulk of the silane. The use of triisopropylsilane as a reducing agent gives >35:1 ratio (beta:alpha) of 2.3.4.6-tetra-O-benzyl-beta-1C-phenyl-1-deoxyglucoside. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：3243 / 3247

页数：5

共 16 条

[1] SYNTHESIS OF C-DISACCHARIDES [J].