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

来源：

TETRAHEDRON | 1991年 / 47卷 / 34期

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

页码：6975 / 6982

页数：8

共 3 条

[1] C-STANNYLATED CARBOHYDRATE-DERIVATIVES .3. 1,2-5,6-DI-O-ISOPROPYLIDENE-3-C-(ORGANOSTANNYL)METHYL-ALPHA-D-ALLOFURANOSE DERIVATIVES - CRYSTAL AND MOLECULAR-STRUCTURE OF 3-C-(DIBUTYLIODOSTANNYL)-METHYL-1,2-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-ALLOFURANOSE
COX, PJ
DOIDGEHARRISON, SMSV
HOWIE, RA
NOWELL, IW
TAYLOR, OJ
WARDELL, JL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (11): : 2017 - 2022
[2] C-STANNYLATED CARBOHYDRATE-DERIVATIVES .5. 1,2-5,6-DI-O-ISOPROPYLIDENE-3-C-(ORGANOSTANNYL)METHYL-ALPHA-D-ALLOFURANOSE AND 1,2-5,6-DI-O-ISOPROPYLIDENE-3-C-(PHENYLSTANNYL)METHYL-ALPHA-D-ALLOFURANOSE COMPOUNDS - X-RAY CRYSTAL AND MOLECULAR-STRUCTURE OF 1,2-5,6-DI-O-ISOPROPYLIDENE-3-C-(TRIPHENYLSTANNYLMETHYL)-ALPHA-D-ALLOFURANOSE
BURNETT, LA
DOIDGEHARRISON, SMSV
GARDEN, SJ
HOWIE, RA
TAYLOR, OJ
WARDELL, JL
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1993, (14): : 1621 - 1628
[3] BRANCHED-CHAIN SUGARS .15. THE CRYSTAL-STRUCTURE OF 3-C-[(R)-(1-HYDROXY-2-PHTHALIMIDOETHYL)]-1,2-5,6-DI-O-ISOPROPYLIDENE-ALPHA-D-ALLOFURANOSE AND RELATED STUDIES
BRIMACOMBE, JS
HANNA, R
WEAKLEY, TJR
[J]. CARBOHYDRATE RESEARCH, 1983, 123 (01) : 145 - 152

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