Convenient, in situ generation of anhydrous hydrogen iodide for the preparation of α-glycosyl iodides and vicinal iodohydrins and for the catalysis of Ferrier glycosylation

被引：40

作者：

Chervin, SM ^{[1
]}

Abada, P ^{[1
]}

Koreeda, M ^{[1
]}

机构：

[1] Univ Michigan, Dept Chem, Ann Arbor, MI 48109 USA

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 03期

关键词：

D O I：

10.1021/ol991312d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Anhydrous hydrogen iodide is generated in situ by the reaction of solid iodine and a thiol, The HI thus generated has been employed for the efficient preparation of alpha-glycosyl iodides and vicinal iodohydrins from the corresponding glycosyl acetates and epoxides, respectively, and for Ferrier glycosylation of alcohols and thiols.

引用

页码：369 / 372

页数：4

共 36 条

[1] Amaratunga W, 1998, J POLYM SCI POL CHEM, V36, P379
[2] A HIGHLY REGIOSELECTIVE CONVERSION OF EPOXIDES TO HALOHYDRINS BY LITHIUM HALIDES
BAJWA, JS
ANDERSON, RC
[J]. TETRAHEDRON LETTERS, 1991, 32 (26) : 3021 - 3024
[3] I(PY)2BF4, A NEW REAGENT IN ORGANIC-SYNTHESIS - GENERAL-METHOD FOR THE 1,2-IODOFUNCTIONALIZATION OF OLEFINS
BARLUENGA, J
GONZALEZ, JM
CAMPOS, PJ
ASENSIO, G
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1985, 24 (04): : 319 - 320
[4] BROMMFIELD CE, 1997, ORG P RES DEV, V1, P88
[5] COPOZZI G, 1974, CHEM THIOL GROUP, P785
[6] PREPARATION OF GLYCOSYL HALIDES UNDER NEUTRAL CONDITIONS
ERNST, B
WINKLER, T
[J]. TETRAHEDRON LETTERS, 1989, 30 (23) : 3081 - 3084
[7] FARLOW MW, 1948, J BIOL CHEM, V176, P71
[8] SYNTHESIS OF DERIVATIVES OF 3-O-(2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSYL)-L-SERINE AND L-THREONINE
FERRARI, B
PAVIA, AA
[J]. CARBOHYDRATE RESEARCH, 1980, 79 (01) : C1 - C7
[9] UNSATURATED CARBOHYDRATES .9. SYNTHESIS OF 2,3-DIDEOXY-ALPHA-D-ERYTHRO-HEX-2-ENOPYRANOSIDES FROM TRI-O-ACETYL-D-GLUCAL
FERRIER, RJ
PRASAD, N
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (04): : 570 - &
[10] Ferrier RJ, 1995, MONOSACCHARIDES THEI, P60

← 1 2 3 4 →