SYNTHESIS OF BETA-MANNOPYRANOSIDES FROM ALPHA-EPIMERS BY RADICAL INVERSION - 1,6-HYDROGEN TRANSFER-REACTIONS OF 2-O-(2-BROMOARYL)DIMETHYLSILYL-ALPHA-METHYL-D-MANNOPYRANOSIDES

被引：56

作者：

YAMAZAKI, N ^{[1
]}

EICHENBERGER, E ^{[1
]}

CURRAN, DP ^{[1
]}

机构：

[1] UNIV PITTSBURGH,DEPT CHEM,PITTSBURGH,PA 15260

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(00)73451-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Intramolecular hydrogen transfer reactions of 3-O-acyl-alpha-methyl-D-mannopyranosides occur in a 1,6-fashion to give inverted beta-mannopyranosides. The yields are limited by competing 1,5-hydrogen transfer reactions that give isomeric alpha-glucopyranosides.

引用

页码：6623 / 6626

页数：4

共 24 条

[1] STEREOELECTRONIC EFFECTS IN HYDROGEN-ATOM ABSTRACTION FROM SUBSTITUTED 1,3-DIOXANES
BECKWITH, ALJ
EASTON, CJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (03) : 615 - 619
[2] INTRAMOLECULAR HYDROGEN-ATOM ABSTRACTION IN CARBOHYDRATES AND NUCLEOSIDES - INVERSION OF AN ALPHA-MANNOPYRANOSIDE TO BETA-MANNOPYRANOSIDE AND GENERATION OF THYMIDINE C-4' RADICALS
BRUNCKOVA, J
CRICH, D
YAO, QW
[J]. TETRAHEDRON LETTERS, 1994, 35 (36) : 6619 - 6622
[3] THE SYNTHESIS AND REACTIONS OF ORTHO-BROMOPHENYLLITHIUM
CHEN, LS
CHEN, GJ
TAMBORSKI, C
[J]. JOURNAL OF ORGANOMETALLIC CHEMISTRY, 1980, 193 (03) : 283 - 292
[4] SEQUENTIAL DIASTEREOSELECTIVE FREE-RADICAL REACTIONS - SYNTHESIS OF AN ADVANCED OLIVOMYCIN-A C-D-DISACCHARIDE
CRICH, D
HERMANN, F
[J]. TETRAHEDRON LETTERS, 1993, 34 (21) : 3385 - 3388
[5] CURRAN DP, 1992, SYNTHESIS-STUTTGART, P123
[6] 1,2-ASYMMETRIC INDUCTION IN RADICAL REACTIONS - DEUTERATION AND ALLYLATION REACTIONS OF BETA-OXY-O-IODOANILIDES
CURRAN, DP
ABRAHAM, AC
[J]. TETRAHEDRON, 1993, 49 (22) : 4821 - 4840
[7] RADICAL TRANSLOCATION REACTIONS OF VINYL RADICALS - SUBSTITUENT EFFECTS ON 1,5-HYDROGEN-TRANSFER REACTIONS
CURRAN, DP
SHEN, W
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (14) : 6051 - 6059
[8] INTRAMOLECULAR HYDROGEN TRANSFER-REACTIONS OF ORTHO-(BROMOPHENYL)DIALKYLSILYL ETHERS - PREPARATION OF RAPAMYCIN-D1
CURRAN, DP
SOMAYAJULA, KV
YU, HS
[J]. TETRAHEDRON LETTERS, 1992, 33 (17) : 2295 - 2298
[9] ATOM TRANSFER CYCLIZATION REACTIONS OF ALPHA-IODO ESTERS, KETONES, AND MALONATES - EXAMPLES OF SELECTIVE 5-EXO, 6-ENDO, 6-EXO, AND 7-ENDO RING CLOSURES
CURRAN, DP
CHANG, CT
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1989, 54 (13) : 3140 - 3157
[10] CURRAN DP, 1994, IN PRESS TETRAHEDRON

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