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使用 Passerini 反应合成 d-吡喃葡萄糖苷衍生的缩肽。

Synthesis of d-glycopyranosyl depsipeptides using Passerini reaction.

机构信息

Bioorganic Laboratory, Department of Chemistry, University of Delhi, Delhi, 110007, India; Department of Chemistry, Rajdhani College, University of Delhi, Delhi, 110015, India.

Department of Chemistry, St. Stephen's College, University of Delhi, Delhi, 110007, India.

出版信息

Carbohydr Res. 2021 Feb;500:108236. doi: 10.1016/j.carres.2021.108236. Epub 2021 Jan 11.

Abstract

A protocol based on Passerini multi-component reaction has been developed for facile, efficient and atom economical synthesis of a small library of twenty potential bioactive (2R)-2-(d-glycopyranosyl)-2-acyloxyacetamides using perbenzylated d-glycopyranosyl aldehydes, substituted isocyanides and different aliphatic/aromatic carboxylic acids. All twenty synthesized d-glycopyranosyl α-acyloxy amides, commonly known as depsipeptides were unambiguously identified on the basis of their spectral (IR, H, C NMR, COSY, HSQC, NOESY and HRMS) data analysis.

摘要

基于 Passerini 多组分反应的方案已被开发出来,用于简便、高效、原子经济地合成二十个潜在生物活性的(2R)-2-(d-吡喃葡萄糖基)-2-酰氧基乙酰胺小分子库,使用全保护的 d-吡喃葡萄糖醛酸醛、取代异氰化物和不同的脂肪族/芳香族羧酸。所有合成的二十个 d-吡喃葡萄糖基α-酰氧基酰胺,通常称为 depsipeptides,根据它们的光谱(IR、H、C NMR、COSY、HSQC、NOESY 和 HRMS)数据分析得到了明确的鉴定。

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