Transformation in carbohydrate chemistry, Part 5. An efficient one step dihydroxylation of 1,2-glycals with oxone in acetone

被引：34

作者：

Rani, S ^{[1
]}

Vankar, YD ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Kanpur 208016, Uttar Pradesh, India

来源：

TETRAHEDRON LETTERS | 2003年 / 44卷 / 05期

关键词：

STEREOCONTROLLED SYNTHESIS; C-GLYCOSIDES; CONVERSION;

D O I：

10.1016/S0040-4039(02)02774-0

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A number of glycals have been converted into the corresponding 1,2-diols in fair to good yields. The reaction appears to proceed via the corresponding epoxide which opens in situ. (C) 2003 Elsevier Science Ltd. All rights reserved.

引用

页码：907 / 909

页数：3

共 18 条

[1] SYNTHESIS OF BETA-MANNOPYRANOSIDES BY INTRAMOLECULAR AGLYCON DELIVERY
BARRESI, F
HINDSGAUL, O
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9376 - 9377
[2] BOLS M, 1992, CHEM COMMUN, P913
[3] A NEW METHOD OF ANOMERIC PROTECTION AND ACTIVATION BASED ON THE CONVERSION OF GLYCOSYL AZIDES INTO GLYCOSYL FLUORIDES
BRODER, W
KUNZ, H
[J]. CARBOHYDRATE RESEARCH, 1993, 249 (01) : 221 - 241
[4] Stereospecific synthesis of α- and β-C-glycosides from glycosyl sulfoxides:: Scope and limitations
Carpintero, M
Nieto, I
Fernández-Mayoralas, A
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) : 1768 - 1774
[5] CARBOHYDRATES AS CHIRAL AUXILIARIES - SYNTHESIS OF 2-HYDROXY-BETA-D-GLUCOPYRANOSIDES
CHARETTE, AB
MARCOUX, JF
COTE, B
[J]. TETRAHEDRON LETTERS, 1991, 32 (49) : 7215 - 7218
[6] Total synthesis of caloporoside
Fürstner, A
Konetzki, I
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1998, 63 (09) : 3072 - 3080
[7] ON THE DIRECT EPOXIDATION OF GLYCALS - APPLICATION OF A REITERATIVE STRATEGY FOR THE SYNTHESIS OF BETA-LINKED OLIGOSACCHARIDES
HALCOMB, RL
DANISHEFSKY, SJ
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (17) : 6661 - 6666
[8] Samarium diiodide mediated coupling of glycosyl phosphates with carbon radical or anion acceptors - Synthesis of C-glycosides
Hung, SC
Wong, CH
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (22): : 2671 - 2674
[9] Reducing oligosaccharides via glycal assembly: on the remarkable stability of anomeric hydroxyl groups to global deprotection with sodium in liquid ammonia
Iserloh, U
Dudkin, V
Wang, ZG
Danishefsky, SJ
[J]. TETRAHEDRON LETTERS, 2002, 43 (39) : 7027 - 7030
[10] 3,4,6-TRI-O-BENZYL-ALPHA-D-ARABINO-HEXOPYRANOS-2-ULOSYL BROMIDE - A VERSATILE GLYCOSYL DONOR FOR THE EFFICIENT GENERATION OF BETA-D-MANNOPYRANOSIDIC LINKAGES
LICHTENTHALER, FW
SCHNEIDERADAMS, T
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) : 6728 - 6734

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