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使用普林斯环化反应立体选择性合成2-脱氧-β-C-芳基/烷基糖苷：在C-二糖和不同保护的C-芳基糖苷合成中的应用。

Stereoselective synthesis of 2-deoxy-β-C-aryl/alkyl glycosides using Prins cyclization: Application in the synthesis of C-disaccharides and differently protected C-aryl glycosides.

作者信息

Dubbu Sateesh, Chennaiah Ande, Verma Ashish Kumar, Vankar Yashwant D

机构信息

Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.

Department of Chemistry, Indian Institute of Technology Kanpur, Kanpur, 208016, India.

出版信息

Carbohydr Res. 2018 Oct;468:64-68. doi: 10.1016/j.carres.2018.08.013. Epub 2018 Aug 22.

DOI:10.1016/j.carres.2018.08.013
PMID:30153553
Abstract

2-Deoxy-β-C-aryl/alkyl glycosides were synthesized from di-O-pivaloyl protected homoallylic alcohol derived from D-mannitol with various aldehydes via the Prins cyclization. The salient features of this methodology are high yields and excellent stereoselectivity. This method has also been successfully applied to the synthesis of differently protected 2-deoxy-β-C-aryl glycosides and C-disaccharides. One of the 2-deoxy-β-C-aryl glycosides was utilized as a glycosyl acceptor in the glycosylation to synthesize an O-linked disaccharides.

摘要

以D-甘露糖醇衍生的二-O-新戊酰基保护的高烯丙醇与各种醛通过普林斯环化反应合成了2-脱氧-β-C-芳基/烷基糖苷。该方法的显著特点是产率高和立体选择性优异。该方法还成功应用于不同保护的2-脱氧-β-C-芳基糖苷和C-二糖的合成。其中一种2-脱氧-β-C-芳基糖苷被用作糖基化反应中的糖基受体，以合成O-连接的二糖。

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