钯催化交叉偶联反应引入不饱和亚糖C2位结构多样性

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-06-23 DOI:10.1002/ejoc.202500502

Yves Bleriot, angelique ferry, quentin joachim, delphine carry, mattéo di pasquale, jerome marrot, jacques uziel, nadege lubin-germain, Jerome desire, atsushi kato, suzuka yamamoto

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引用次数: 0

摘要

为了改变亚氨基糖在C2位置的功能，从糖内酰胺中有效地合成了D -葡萄糖、D -半乳和D -木糖系列中的2 -碘亚氨基糖。他们的温和钯催化氨基羰基化、芳基化和膦基化是成功的，并提供了一系列C2功能化的亚氨基糖。其中两种化合物被O -去保护以提供1,2 -不饱和亚糖，这些亚糖被证明是糖苷酶的适度抑制剂。

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Introduction of Structural Diversity at the C2 Position of Unsaturated Iminosugars through Palladium‐Catalysed Cross‐Coupling Reactions

To vary the functionality of iminosugars at the C2 position, protected 2‐iodoiminoglycals in the D‐gluco, D‐galacto and D‐xylo series were efficiently synthesized from sugar lactams. Their mild palladium‐catalyzed aminocarbonylation, arylation and phosphonylation were successful and provided a range of C2‐functionalized iminoglycals in good yields. Two of these compounds were O‐deprotected to afford 1,2‐unsaturated iminosugars that proved to be modest inhibitors of glycosidases.

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.