半纤维素C5糖的立体选择性乙酰化

Stereoselective acetylation of hemicellulosic C5-sugars.

作者信息

Herde Zachary D, John Prathap D, Alvarez-Fonseca Dania, Satyavolu Jagannadh, Burns Christopher T

机构信息

Conn Center for Renewable Energy Research, University of Louisville, Louisville, KY, 40292, USA.

Department of Chemistry, University of Louisville, 2320 South Brook Street, Louisville, KY, 40292, USA; Conn Center for Renewable Energy Research, University of Louisville, Louisville, KY, 40292, USA.

出版信息

Carbohydr Res. 2017 Apr 18;443-444:1-14. doi: 10.1016/j.carres.2017.03.008. Epub 2017 Mar 10.

DOI:10.1016/j.carres.2017.03.008

PMID:28319681

Abstract

The stereoselective peracetylation of α-d-xylose (1) and α-l-arabinose (4) using a combination of triethylamine and acetic anhydride in the presence or absence of a catalytic amount of dimethylaminopyridine (DMAP) is described. The peracetylated d-xylose and l-arabinose alpha pyranose anomers 2α and 5α are obtained in 97% and 56% yields respectively. The peracetylated d-xylose beta pyranose anomer 2β is obtained in 71% yield through simple modification of the reaction conditions. Details regarding synthesis and isolation optimization studies under different conditions are presented below. The stereoselective peracetylation reactions disclosed here have been used to separate mixtures of d-xylose and l-arabinose as their peracetylated derivatives 2β and 5α in 47% and 42% yields and can provide pure pentoses after deacetylation.

摘要

描述了在有或没有催化量的二甲基氨基吡啶（DMAP）存在下，使用三乙胺和乙酸酐的组合对α - D - 木糖（1）和α - L - 阿拉伯糖（4）进行立体选择性全乙酰化反应。全乙酰化的D - 木糖和L - 阿拉伯糖α - 吡喃糖端基异构体2α和5α的产率分别为97%和56%。通过简单改变反应条件，全乙酰化的D - 木糖β - 吡喃糖端基异构体2β的产率为71%。以下介绍了不同条件下合成和分离优化研究的详细情况。本文所公开的立体选择性全乙酰化反应已用于分离D - 木糖和L - 阿拉伯糖的混合物，得到其全乙酰化衍生物2β和5α，产率分别为47%和42%，脱乙酰化后可得到纯戊糖。