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 [J].

BARRESI, F ;

HINDSGAUL, O .

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 [J].

BRODER, W ;

KUNZ, H .

CARBOHYDRATE RESEARCH, 1993, 249 (01) :221-241

[4] Stereospecific synthesis of α- and β-C-glycosides from glycosyl sulfoxides:: Scope and limitations [J].

Carpintero, M ;

Nieto, I ;

Fernández-Mayoralas, A .

JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (05) :1768-1774

[5] CARBOHYDRATES AS CHIRAL AUXILIARIES - SYNTHESIS OF 2-HYDROXY-BETA-D-GLUCOPYRANOSIDES [J].

CHARETTE, AB ;

MARCOUX, JF ;

COTE, B .

TETRAHEDRON LETTERS, 1991, 32 (49) :7215-7218

[6] Total synthesis of caloporoside [J].

Fürstner, A ;

Konetzki, I .

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 [J].

HALCOMB, RL ;

DANISHEFSKY, SJ .

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 [J].

Hung, SC ;

Wong, CH .

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 [J].

Iserloh, U ;

Dudkin, V ;

Wang, ZG ;

Danishefsky, SJ .

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 [J].

LICHTENTHALER, FW ;

SCHNEIDERADAMS, T .

JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (22) :6728-6734

← 1 2 →