Gram-scale syntheses of the (1 → 3)-linked and (1 → 4)-linked hyaluronan disaccharides

被引：13

作者：

Adamski-Werner, SL ^{[1
]}

Yeung, BKS ^{[1
]}

Miller-Deist, LA ^{[1
]}

Petillo, PA ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Urbana, IL 61801 USA

来源：

CARBOHYDRATE RESEARCH | 2004年 / 339卷 / 07期

基金：

美国国家卫生研究院;

关键词：

carbohydrates; hyaluronan; oligosaccharides; large-scale synthesis;

D O I：

10.1016/j.carres.2004.03.005

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：

The first gram-scale syntheses of two hyaluronan disaccharides are described. Construction of the (1 --> 4)-linked disaccharide 12 was achieved in 12% overall yield using 2,3-bis-dimethyl acetal protection in combination with chlorosilane-induced carbamate cleavage methodologies. The uronic acid functionality was installed using TEMPO oxidation with NaOCl as the hypochlorite source. The (1 --> 3)-linked disaccharide 18 was achieved in 7% overall yield utilizing acetonide protection in addition to the chlorosilane-induced carbamate cleavage methodology and the TEMPO oxidation. (C) 2004 Elsevier Ltd. All rights reserved.

引用

收藏

页码：1255 / 1262

页数：8

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