INTRAMOLECULAR HYDROGEN-ATOM ABSTRACTION IN CARBOHYDRATES AND NUCLEOSIDES - INVERSION OF AN ALPHA-MANNOPYRANOSIDE TO BETA-MANNOPYRANOSIDE AND GENERATION OF THYMIDINE C-4' RADICALS

被引：48

作者：

BRUNCKOVA, J ^{[1
]}

CRICH, D ^{[1
]}

YAO, QW ^{[1
]}

机构：

[1] UNIV ILLINOIS,DEPT CHEM,CHICAGO,IL 60607

来源：

TETRAHEDRON LETTERS | 1994年 / 35卷 / 36期

关键词：

D O I：

10.1016/S0040-4039(00)73450-2

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Treatment of 1-bromo-2-methyl-2-propyl ether derivatives of alcohols with Bu(3)SnH(D) results in 1,5-Hydrogen abstraction reactions: the system is applied to the inversion of an alpha- to beta-mannoside and to the formation of nucleoside C4' radicals.

引用

页码：6619 / 6622

页数：4

共 44 条

[1] AKHTAR M, 1964, ADV PHOTOCHEM, V2, P263
[2] SYNTHESIS OF BETA-MANNOPYRANOSIDES BY INTRAMOLECULAR AGLYCON DELIVERY
BARRESI, F
HINDSGAUL, O
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9376 - 9377
[3] BARTON DHR, 1968, PURE APPL CHEM, V16, P1
[4] AN ELECTRON-SPIN RESONANCE INVESTIGATION OF FREE-RADICALS WITH OXYGEN-CONTAINING AND SULFUR-CONTAINING SUBSTITUENTS
BECKWITH, ALJ
BRUMBY, S
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12): : 1801 - 1807
[5] 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
[6] THE MECHANISM OF THE BETA-ACYLOXYALKYL RADICAL REARRANGEMENT .2. BETA-ACYLOXYTETRAHYDROPYRANYL RADICALS
BECKWITH, ALJ
DUGGAN, PJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (09): : 1673 - 1679
[7] BROWN CDS, 1993, TETRAHEDRON LETT, V34, P127
[8] KINETIC APPLICATIONS OF ELECTRON-PARAMAGNETIC RESONANCE SPECTROSCOPY .26. QUANTUM-MECHANICAL TUNNELING IN ISOMERIZATION OF STERICALLY HINDERED ARYL RADICALS
BRUNTON, G
GRILLER, D
BARCLAY, LRC
INGOLD, KU
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (22) : 6803 - 6811
[9] ORGANOSILANES AS RADICAL-BASED REDUCING AGENTS IN SYNTHESIS
CHATGILIALOGLU, C
[J]. ACCOUNTS OF CHEMICAL RESEARCH, 1992, 25 (04) : 188 - 194
[10] STEREOSELECTIVE FREE-RADICAL REACTIONS IN THE PREPARATION OF 2-DEOXY-BETA-D-GLUCOSIDES
CRICH, D
RITCHIE, TJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1988, (22) : 1461 - 1463

← 1 2 3 4 5 →