Stereoselective synthesis of a ketohexofuranose from an aldohexopyranose by a [6+1-1] strategy

被引：11

作者：

Babu, BS ^{[1
]}

Balasubramanian, KK ^{[1
]}

机构：

[1] Indian Inst Technol, Dept Chem, Madras 600036, Tamil Nadu, India

来源：

CARBOHYDRATE RESEARCH | 2005年 / 340卷 / 04期

关键词：

glycal; fructofuranose; deuterated fructofuranose; ozonolysis; isotopic labelling; ketohexofuranose; aldohexopyranose;

D O I：

10.1016/j.carres.2005.01.008

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Ozonolysis of 2-acetoxymethyl-1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-D-aribino-hex-1-enitol gave 1-O-acetyl-3,4,6-tri-O-benzyl-4-O-formyl-D-arabino-hex-2-ulose (5). Subsequent hydrolysis and acetylation of 5 provided 1,2-di-O-acetyl-3,4,6-tri-O-benzyl-D-fructofuranose 6 in excellent yield. This methodology allows specific deuteration at C-1 of a protected D-fructofuranose derivative. This approach therefore could serve as [6+1-1] formulation for hexose series inter-conversion, that is, aldohexopyranose to ketohexofuranose. (c) 2005 Elsevier Ltd. All rights reserved.

引用

页码：753 / 758

页数：6