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吡喃葡萄糖醛:有机合成中新兴的手性合成子。

-Glycopyranosyl aldehydes: emerging chiral synthons in organic synthesis.

作者信息

Kumar Sandeep, Khatri Vinod, Mangla Priyanka, Chhatwal Rajni Johar, Parmar Virinder S, Prasad Ashok K

机构信息

Bioorganic Laboratory, Department of Chemistry, University of Delhi Delhi India

T. D. L. Govt College for Women Murthal-131027 Haryana India.

出版信息

RSC Adv. 2023 Jul 3;13(29):19898-19954. doi: 10.1039/d3ra02122j. eCollection 2023 Jun 29.

Abstract

Herein, we have summarized the vast array of synthetic processes that have been developed for the synthesis of -glycopyranosyl aldehydes and diverse -glycoconjugates derived from them by covering the literature reported from 1979 to 2023. Notwithstanding its challenging chemistry, -glycosides are considered stable pharmacophores and are used as important bioactive molecules. The discussed synthetic methodologies to access -glycopyranosyl aldehydes take advantage of seven key intermediates, allene, thiazole, dithiane, cyanide, alkene, and nitromethane. Furthermore, the integration of complex -glycoconjugates derived from varied -glycopyranosyl aldehydes involves nucleophilic addition/substitution, reduction, condensation, oxidation, cyclo condensation, coupling, and Wittig reactions. In this review, we have categorized the synthesis of -glycopyranosyl aldehydes and -glycoconjugates on the basis of the methodology used for their synthesis and on types of -glycoconjugates, respectively.

摘要

在此,我们通过涵盖1979年至2023年报道的文献,总结了为合成α-吡喃糖基醛及其衍生的各种α-糖缀合物而开发的大量合成方法。尽管α-糖苷化学具有挑战性,但它被认为是稳定的药效基团,并被用作重要的生物活性分子。所讨论的合成α-吡喃糖基醛的方法利用了七种关键中间体,即丙二烯、噻唑、二硫烷、氰化物、烯烃和硝基甲烷。此外,源自各种α-吡喃糖基醛的复杂α-糖缀合物的合成涉及亲核加成/取代、还原、缩合、氧化、环缩合、偶联和维蒂希反应。在本综述中,我们分别根据合成α-吡喃糖基醛和α-糖缀合物所用的方法以及α-糖缀合物的类型对其合成进行了分类。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7631/10316784/0a547e58d945/d3ra02122j-f1.jpg

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