Stereoselective synthesis of conformationally constrained cyclohexanediols: A set of molecular scaffolds for the synthesis of glycomimetics

被引：38
|
作者：
Bernardi, A
Arosio, D
Manzoni, L
Micheli, F
Pasquarello, A
Seneci, P
机构：
[1] Univ Milan, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
[2] GlaxoWellcome SpA, Med Res Ctr, I-37100 Verona, Italy
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2001年 / 66卷 / 19期
关键词：
D O I：
10.1021/jo015570b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The practical, stereoselective synthesis of the three diastereoisomeric 1,2-trans-dicarboxy-4,5-cyclohexanediols. 1-3 (DCCHDs) is described, starting from a common precursor, easily available in both enantiomeric forms. The regioselective derivatization of all functional groups of I is also reported. The three DCCHDs are locked in a single chair conformation and thus can be used to mimic vicinally disubstituted monosaccharides of any relative configuration.
引用
收藏
页码：6209 / 6216
页数：8
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