An improved synthesis of 3,6-anhydro-D-glucal and a study of its unusual chemical reactivity

被引：1

作者：

Basava, Vikram ^{[1
]}

Gorun, Sergiu M. ^{[1
]}

Marzabadi, Cecilia H. ^{[1
]}

机构：

[1] Seton Hall Univ, Dept Chem & Biochem, S Orange, NJ 07079 USA

来源：

CARBOHYDRATE RESEARCH | 2014年 / 391卷

关键词：

3; 6-Anhydro-D-glucal; 6-O-Tosyl-D-glucal; Addition reactions; Dianhydride sugar; CARBOHYDRATE-DERIVATIVES; AMMONIUM-NITRATE; SUGAR; RECEPTOR; DESIGN; ACID;

D O I：

10.1016/j.carres.2014.03.005

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：

6-O-Tosyl-D-glucal 1 upon treatment with excess LiAlH4 unexpectedly gave 3,6-anhydro-D-glucal 2 as a major product in good yield. A crystal structure was obtained. Reaction of the anhydride 2 with N-iodosuccinimide (NIS) in excess methanol resulted in the formation of diastereomeric 2-deoxy-2-iodoglycosides. Addition of ceric (IV) ammonium nitrate and thiophenol to a solution of 2 in acetonitrile gave a mixture of 2-deoxy and 2,3-unsaturated thioglycosides. Reaction of 1,2: 3,4-di-O-isopropylidine-alpha-D-galactopyranose with the anhydro sugar 2 in the presence of N-iodosuccinimide did not give the expected iodoglycoside mixture, but instead gave an unusual 1,4: 3,6-dianhydride 7 as the major product. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：106 / 111

页数：6

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