山葵硫化物的合成及结构修正：从山葵中分离的二硫化物葡萄糖基

IF 2.2 3区化学 Q2 CHEMISTRY, ORGANIC

Tetrahedron Pub Date : 2025-08-25 DOI:10.1016/j.tet.2025.134900

Kenji Kimura, Shinnosuke Wakamori, Ryo Katsuta, Ken Ishigami

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引用次数: 0

摘要

首次成功地合成了三种天然葡萄糖基二硫化物- wasulfisides A、B和3-epi- wasulfisides B。这些化合物最初是从山葵（Eutrema japonicum）中分离出来的，具有罕见的天然β-葡萄糖基二硫化基序。核心结构通过β-糖基硫代糖酸酯与多种硫醇之间形成S-S键有效构建。从d-葡萄糖开始，总产率达到37%。因此，基于其区域异构体和立体异构体的合成，成功地修改了含有氧二硫辛酸的独特化合物wasulfiside A的结构。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Synthesis and structure revision of wasulfisides: glucosyl disulfides isolated from wasabi

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Synthesis and structure revision of wasulfisides: glucosyl disulfides isolated from wasabi

The first syntheses of three natural glucosyl disulfides—wasulfisides A, B, and 3-epi-wasulfiside B—were successfully accomplished. These compounds were originally isolated from wasabi (Eutrema japonicum) and possess a rare natural β-glucosyl disulfide motif. The core structure was efficiently constructed via S–S bond formation between a β-glucosyl thiotosylate and various thiols. The overall yields reached 37%, starting from d-glucose. Accordingly, the structure of wasulfiside A, a unique oxadithiocine-containing compound, was successfully revised based on the syntheses of its regio- and stereoisomers.

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来源期刊

Tetrahedron 化学-有机化学

CiteScore

3.90

自引率

4.80%

发文量

439

审稿时长

34 days

期刊介绍： Tetrahedron publishes full accounts of research having outstanding significance in the broad field of organic chemistry and its related disciplines, such as organic materials and bio-organic chemistry. Regular papers in Tetrahedron are expected to represent detailed accounts of an original study having substantially greater scope and details than that found in a communication, as published in Tetrahedron Letters. Tetrahedron also publishes thematic collections of papers as special issues and ''Reports'', commissioned in-depth reviews providing a comprehensive overview of a research area.