Molecular Iodine-Mediated β-Glycosylation of Thiomannosides with 1,6-Anhydrosugars

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2025-03-03 DOI:10.1021/acs.orglett.5c00388
Ahmed Atito, Jasper S. Dumalaog, Kuei-Yao Tseng, Yen-Ju Ting, Medel Manuel L. Zulueta, Shang-Cheng Hung
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Abstract

β-Mannosides play a crucial role in cellular processes and immune responses, and their synthesis remains one of the most challenging tasks in carbohydrate chemistry. Glycosyl donors, such as thiomannosides, are stable and compatible with a range of protection and deprotection conditions. In this study, we demonstrate that molecular iodine efficiently induces the activation and coupling of thiomannosides with various 1,6-anhydrosugars as acceptors. This method provides mild activation conditions and high β-stereoselectivity for the synthesis of multiple β-mannosides.

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分子碘介导的硫甘烷苷与1,6-无水糖的β-糖基化
β-甘露糖苷在细胞过程和免疫反应中起着至关重要的作用,它们的合成仍然是碳水化合物化学中最具挑战性的任务之一。糖基供体,如硫甘烷苷,是稳定的,与一系列保护和去保护条件兼容。在这项研究中,我们证明了分子碘能有效地诱导以各种1,6-无水糖为受体的硫甘烷苷的激活和偶联。该方法为合成多种β-甘露糖苷提供了温和的活化条件和高的β立体选择性。
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来源期刊
Organic Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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