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α-和β-D-吡喃葡萄糖基脲的立体有择合成。

Stereospecific synthesis of the alpha- and beta-D-glucopyranosyl ureas.

作者信息

Ichikawa Y, Nishiyama T, Isobe M

机构信息

Laboratory of Organic Chemistry, School of Bioagricultural Sciences, Nagoya University, Chikusa, Nagoya 464-8601, Japan.

出版信息

J Org Chem. 2001 Jun 15;66(12):4200-5. doi: 10.1021/jo0100751.

Abstract

A new, one-pot, two-stage procedure for the preparation of the alpha- and beta-D-glucopyranosyl ureas has been developed. Oxidation of glucopyranosyl isocyanides provides glucopyranosyl isocyanates, which can be trapped in situ with amines to afford good yields of glucopyranosyl ureas. Application of this method establishes the successful synthesis of the hitherto unknown N,N'-di-alpha,alpha- and alpha,beta-D-glucopyranosyl ureas.

摘要

已开发出一种用于制备α-和β-D-吡喃葡萄糖基脲的新型一锅两步法。吡喃葡萄糖基异腈的氧化生成吡喃葡萄糖基异氰酸酯,其可在原位与胺捕获,以高产率得到吡喃葡萄糖基脲。该方法的应用成功合成了迄今未知的N,N'-二-α,α-和α,β-D-吡喃葡萄糖基脲。

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