Convenient synthesis of 2,3-O-isopropylidene-5-thio-D-ribose and 5-thio-D-ribose;: synthesis of 1,4-anhydro-2,3-O-isopropylidene-α-D-ribopyranose and 1,4-anhydro-2,3-O-isopropylidene-5-thio-α-D-ribopyranose

被引：14

作者：

Fleetwood, A ^{[1
]}

Hughes, NA ^{[1
]}

机构：

[1] Univ Newcastle Upon Tyne, Dept Chem, Newcastle Upon Tyne NE1 7RU, Tyne & Wear, England

来源：

CARBOHYDRATE RESEARCH | 1999年 / 317卷 / 1-4期

关键词：

anydro sugar; furanose-pyranose equilibria; methanesulfonate esters; 5-thio-D-ribose derivatives; thio sugars;

D O I：

10.1016/S0008-6215(99)00064-6

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：

Sequential mesylation-acetylation of 2,3-O-isopropylidene-D-ribofuranose gave 1-O-acetyl-2,3-O-isopropylidene-5-O-methanesulfonyl-beta-D-ribofuranose that was converted into 1-O-acetyl-5-(S)-acetyl-2,3-O-isopropylidene-5-thio-beta-D-ribose, deacetylation of which gave 2,3-O-isopropylidene-5-thio-D-ribose as the beta-pyranose form, which was hydrolysed to 5-thio-D-ribose. 1,4-Anhydro-2,3-O-isopropylidene-alpha-D-ribopyranose was obtained by sodium methoxide treatment of 1-O-acetyl-2,3-O-isopropylidene-5-O-methanesulfonyl-beta-D-ribofuranose and 1,4-anhydro-2,3-O-isopropylidene-5-thio-alpha-D-ribopyranose was similarly synthesised via 1-(S)-acetyl-2,3-O-isopropylidene-5-O-methanesulfonyl-5-thio-alpha-D-ribofuranose. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：204 / 209

页数：6

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