由D-戊糖-1,4-内酯高效合成1-S-烷基-1-硫代-L-核糖醇、D-来苏糖醇和L-木糖醇。

Efficient syntheses of 1-S-alkyl-1-thio-L-ribitols, D-lyxitols and L-xylitols from D-pentono-1,4-lactones.

作者信息

Lalot J, Manier G, Stasik I, Demailly G, Beaupère D

机构信息

Laboratoire des Glucides, Université de Picardie Jules Verne, 33 rue Saint-Leu, F-80039 Amiens, France.

出版信息

Carbohydr Res. 2001 Sep 21;335(1):55-61. doi: 10.1016/s0008-6215(01)00204-x.

DOI:10.1016/s0008-6215(01)00204-x

PMID:11553354

Abstract

The thioalkylation of unprotected 5-bromo-5-deoxy-D-ribono, D-arabinono, and D-xylono-1,4-lactone was performed with the alkylthiol-sodium hydride reagent. The corresponding 5-S-alkyl-5-thio-D-pentono-1,4-lactones were isolated in good yields (82-95%). Reduction with NaBH(4) of these derivatives gave the 1-S-alkyl-1-thio-L-ribitols, D-lyxitols and L-xylitols in 85-96% yields.

摘要

使用烷基硫醇-氢化钠试剂对未保护的5-溴-5-脱氧-D-核糖、D-阿拉伯糖和D-木糖-1,4-内酯进行硫烷基化反应。以良好的产率（82-95%）分离得到相应的5-S-烷基-5-硫代-D-戊糖-1,4-内酯。用硼氢化钠还原这些衍生物，以85-96%的产率得到1-S-烷基-1-硫代-L-核糖醇、D-来苏糖醇和L-木糖醇。