一种立体选择性制备 3-C-糖基化 D-和 L-葡萄醛糖的方法。

An approach to stereoselective preparation of 3-C-glycosylated D- and L-glucals.

机构信息

Department of Chemistry of Natural Compounds, Institute of Chemical Technology, Technická 5, 166 28 Prague 6, Czech Republic.

出版信息

Carbohydr Res. 2010 Feb 11;345(3):352-62. doi: 10.1016/j.carres.2009.11.025. Epub 2009 Dec 4.

DOI:10.1016/j.carres.2009.11.025

PMID:20035928

Abstract

An approach to stereoselective synthesis of alpha- or beta-3-C-glycosylated L- or D-1,2-glucals starting from the corresponding alpha- or beta-glycopyranosylethanals is described. The key step of the approach is the stereoselective cycloaddition of chiral vinyl ethers derived from both enantiomers of mandelic acid. The preparation of 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)methyl]-L-arabino-hex-1-enitol, 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)methyl]-D-arabino-hex-1-enitol, and 1,5-anhydro-4,6-di-O-benzyl-2,3-dideoxy-3-C-[(2,3,4-tri-O-benzyl-alpha-L-fucopyranosyl)methyl]-D-arabino-hex-1-enitol serves as an example of this approach.

摘要

本文描述了一种从相应的α-或β-糖醛基乙醇出发，立体选择性合成α-或β-3-C-糖基-L-或 D-1,2-葡糖醛的方法。该方法的关键步骤是手性乙烯基醚的立体选择性环加成，这些乙烯基醚是由扁桃酸的两种对映异构体衍生而来的。1,5-脱水-4,6-二-O-苄基-2,3-二脱氧-3-C-[(2,3,4,6-四-O-苄基-β-D-葡吡喃糖基)甲基]-L-阿拉伯己-1-烯醇、1,5-脱水-4,6-二-O-苄基-2,3-二脱氧-3-C-[(2,3,4,6-四-O-苄基-β-D-葡吡喃糖基)甲基]-D-阿拉伯己-1-烯醇和 1,5-脱水-4,6-二-O-苄基-2,3-二脱氧-3-C-[(2,3,4-三-O-苄基-α-L-岩藻吡喃糖基)甲基]-D-阿拉伯己-1-烯醇的制备就是这种方法的一个例子。