A novel method for regioselective ring-opening reduction of 4,6-O-benzylidene hexopyranoside derivatives using CoCl2 and BH3•THF

被引：31

作者：

Tani, Shinki ^{[1
]}

Sawadi, Sho ^{[1
]}

Kojima, Masaru ^{[1
]}

Akai, Shoji ^{[1
]}

Sato, Ken-ichi ^{[1
]}

机构：

[1] Kanagawa Univ, Fac Engn, Organ Chem Lab, Kanagawa Ku, Yokohama, Kanagawa 2218686, Japan

来源：

TETRAHEDRON LETTERS | 2007年 / 48卷 / 17期

关键词：

carbohydrates; reductive benzylidene ring-opening; cobalt chloride; borane;

D O I：

10.1016/j.tetlet.2007.02.133

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and facile reductive ring-opening reaction for 4,6-O-benzylidene acetal derivatives of hexopyranosides using CoCl2/BH3 center dot THF gave the corresponding 4-O-benzyl-6-OH derivatives selectively in good yields. This convenient method should allow large-scale synthesis at low cost. (c) 2007 Elsevier Ltd. All rights reserved.

引用

页码：3103 / 3104

页数：2

共 30 条

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TETRAHEDRON LETTERS, 2000, 41 (29) : 5547 - 5551
[2] RING-OPENING OF 2,3-O-BENZYLIDENE, 3,4-O-BENZYLIDENE AND 4,6-O-BENZYLIDENE ACETALS OF PYRANOSIDES BY PHOTOBROMINATION WITH BROMOTRICHLOROMETHANE
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Synlett, 1996, (12)
[5] A NOVEL METHOD FOR THE SELECTIVE REDUCTION OF CARBOHYDRATE 4,6-O-BENZYLIDENE ACETALS
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ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1994, 208 : 229 - ORGN
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Daragics, Katalin
Fuegedi, Peter
TETRAHEDRON LETTERS, 2009, 50 (24) : 2914 - 2916
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JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (10): : 2395 - 2397
[8] REGIOSELECTIVE ALPO4-AL2O3 PROMOTED RING-OPENING OF 2,3-EPOXY ESTERS
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CHEMISTRY LETTERS, 1986, (09) : 1565 - 1568
[9] SOME FURTHER RING-OPENING REACTIONS OF METHYL 4,6-O-BENZYLIDENE-2,3-DIDEOXY-2,3-EPIMINO-ALPHA-D-ALLOPYRANOSIDE AND ITS DERIVATIVES
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Maheswara, Muchchintala
Rao, Kummari Subba Venkata Krishna
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TETRAHEDRON LETTERS, 2008, 49 (11) : 1795 - 1800

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