An efficient conversion of N-acetyl-D-glucosamine to N-acetyl-D-galactosamine and derivatives
An efficient conversion of N-acetyl-D-glucosamine to N-acetyl-D-galactosamine and derivatives
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DOI：
10.1016/j.carres.2010.09.008
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发表时间：
2010-11-22
影响因子：
3.1
通讯作者：
Ling, Chang-Chun
中科院分区：
文献类型：
--
作者：
Feng, Jianhao;Ling, Chang-Chun
2-乙酰氨基-2-脱氧-D-半乳糖（D-GalNAc）是一种重要的单糖，广泛存在于自然界中。然而，与其4-差向异构体2-乙酰氨基-2-脱氧-D-葡萄糖（D-GlcNAc）不同，D-GalNAc从商业来源获得非常昂贵。本文中，我们报道了一种有效的转化，其允许在三个步骤中以58.4-75%的总产率将D-GlcNAc转化为D-GalNAc衍生物7。该方法以大于20-g的规模进行，而不需要色谱法。化合物7的多功能性通过合成几种有用的单糖和含有D-GalNAc残基的硫代二糖来证明。(C)2010爱思唯尔有限公司保留所有权利。
2-Acetamido-2-deoxy-D-galactose (D-GalNAc) is an important monosaccharide widely distributed in nature. However, unlike its 4-epimer, the 2-acetamido-2-deoxy-D-glucose (D-GlcNAc), D-GalNAc is very expensive to obtain from commercial sources. Herein we report an efficient transformation that allows for the conversion of D-GlcNAc to a D-GalNAc derivative 7 in three steps and in 58.4-75% overall yields. The process was carried out on a greater than 20-g scale without the need of chromatography. The versatility of compound 7 was demonstrated by the synthesis of several useful monosaccharides and thiodisaccharides containing a D-GalNAc residue. (C) 2010 Elsevier Ltd. All rights reserved.