DIACETONE GLUCOSE ARCHITECTURE AS A CHIRALITY TEMPLATE .1. CRUCIAL EFFECTS OF THE INTRAMOLECULAR OXYGENS UPON THE LIALH4 REDUCTION OF THE PROPARGYL ALCOHOL OF 3-C-ETHYNYL-1,2-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-ALLOFURANOSE DERIVATIVES

被引:8
作者
KAKINUMA, K
MATSUZAWA, T
EGUCHI, T
机构
[1] Department of Chemistry, Tokyo Institute of Technology O-okayama, Meguro-ku, Tokyo
关键词
LIALH4 REDUCTION OF PROPARGYL ALCOHOL; REGIOCHEMISTRY; REACTIVITY; SEMIEMPIRICAL MO CALCULATION; DIACETONE GLUCOSE;
D O I
10.1016/S0040-4020(01)96152-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The facile as well as regio- and stereoselective reactivity of 3-C-ethynl-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose derivatives for LiAlH4 reduction into the corresponding ethenyl derivatives were investigated. The effect of oxygen atoms on the reduction is discussed by means of semi-empirical MO calculation.
引用
收藏
页码:6975 / 6982
页数:8
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