一种用于合成异头2-硫代葡萄糖二糖、2-硫代 kojibiose 和 2-硫代槐糖的简便方法。

A convenient synthesis for anomeric 2-thioglucobioses, 2-thiokojibiose and 2-thiosophorose.

作者信息

Defaye J, Guillot J M

机构信息

CNRS, Département de Recherche Fondamentale sur la Matière Condensée/SESAM, Centre d'Etudes de Grenoble, France.

出版信息

Carbohydr Res. 1994 Feb 3;253:185-94. doi: 10.1016/0008-6215(94)80064-2.

DOI:10.1016/0008-6215(94)80064-2

PMID:8156547

Abstract

2-S-alpha-D-Glucopyranosyl-2-thio-D-glucopyranose (2-thiokojibiose, 8) and 2-S-beta-D-glucopyranosyl-2-thio-D-glucopyranose (2-thiosophorose, 14) were conveniently prepared by SN2 reaction of the corresponding anomers of 2,3,4,6-tetra-O-acetyl-1-thio-D-glucopyranose with 1,3,4,6-tetra-O-acetyl-2-O-tri-flyl-beta-D-mannopyranose, followed by a deprotection sequence for the anomeric acetate involving conversion into the 1-propenyl glycosides. Alkaline O-deacetylation was followed by smooth hydrolysis of the propenyl group at pH approximately 2.

摘要

2-S-α-D-吡喃葡萄糖基-2-硫代-D-吡喃葡萄糖（2-硫代 kojibiose，8）和 2-S-β-D-吡喃葡萄糖基-2-硫代-D-吡喃葡萄糖（2-硫代槐糖，14）可通过 2,3,4,6-四-O-乙酰基-1-硫代-D-吡喃葡萄糖的相应端基异构体与 1,3,4,6-四-O-乙酰基-2-O-三氟甲磺酰基-β-D-甘露吡喃糖进行 SN2 反应，随后对端基乙酸酯进行脱保护序列，包括转化为 1-丙烯基糖苷来方便地制备。碱性 O-脱乙酰化之后，在 pH 约为 2 时丙烯基进行顺利水解。