乙醛衍生环氧乙烯单锅立体特异性合成 1,4-寡糖

IF 3.7 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

ACS Omega Pub Date : 2024-10-31 DOI:10.1021/acsomega.4c0524710.1021/acsomega.4c05247

Maria Chiara Santangelo, Dalila Iacopini, Lucilla Favero, Riccardo Zecchi, Giuseppe Pieraccini, Sebastiano Di Pietro* and Valeria Di Bussolo*,

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引用次数: 0

摘要

最近，天然存在的线性 1,4-寡糖因其在治疗癌症和神经退行性疾病方面的活性而备受关注。由于需要正交保护/去保护、引入离去基团以及糖基化反应的各种活化形式，线性 1,4-寡糖的经典化学合成策略相当耗时。在此，我们提出了一种新的单锅微波活化乙烯基环氧化糖醛衍生体的重复组装方法，它是一种非催化底物依赖性立体特异性过程，可用于制备β-1,4-d-古洛寡糖和α-1,4-d-甘露寡糖。

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One-Pot Stereospecific Synthesis of 1,4-Oligosaccharides by Glycal-Derived Vinyl Epoxides Assembly

Recently, naturally occurring linear 1,4-glycans have attracted remarkable attention for their activity in cancer and neurodegenerative disease treatment. Classical chemical synthetic strategies for linear 1,4-oligosaccharides are considerably time-consuming due to orthogonal protection/deprotection, the introduction of leaving groups, and various forms of activation of the glycosylation reaction. Herein, we present a new one-pot microwave-activated reiterative assembly of glycal-derived vinyl epoxides in an uncatalyzed substrate-dependent stereospecific process for the preparation of both β-1,4-d-Gulo and α-1,4-d-Manno oligosaccharides.

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来源期刊

ACS Omega Chemical Engineering-General Chemical Engineering

CiteScore

6.60

自引率

4.90%

发文量

3945

审稿时长

2.4 months

期刊介绍： ACS Omega is an open-access global publication for scientific articles that describe new findings in chemistry and interfacing areas of science, without any perceived evaluation of immediate impact.