以苯-1,3-二磺酰氟为介导，从糖基半缩醛合成糖基氟化物

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-21 DOI:10.1021/acs.orglett.4c03968

Soumyadip Dey, Shubhi Dwivedi, Debabrata Giri, Abhijit Sau

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引用次数: 0

摘要

我们开发了一种以苯-1,3-二磺酰氟（S2）为氟化剂，结合碱 DBU（1,8-二氮杂双环[5.4.0]十一-7-烯），在温和条件下从糖基半缩醛合成糖基氟化物的高效方法。这种方法成功合成了 17 种具有各种官能团（包括二糖和脱氧硫酸盐）的糖基氟化物，产率高达 99%。这些合成的糖基氟化物在合成重要的 O-和 C-糖苷中的用途得到了进一步证实。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Benzene-1,3-disulfonyl Fluoride Mediated Synthesis of Glycosyl Fluorides from Glycosyl Hemiacetals

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Benzene-1,3-disulfonyl Fluoride Mediated Synthesis of Glycosyl Fluorides from Glycosyl Hemiacetals

We developed an efficient method for synthesizing glycosyl fluorides from glycosyl hemiacetals using benzene-1,3-disulfonyl fluoride (S2) as the fluorinating agent in combination with the base DBU (1,8-diazabicyclo[5.4.0]undec-7-ene) under mild conditions. This approach enabled the successful synthesis of 17 glycosyl fluorides with various functional groups, including disaccharides and deoxysulfates, with yields of up to 99%. The utility of these synthesized glycosyl fluorides was further demonstrated in the synthesis of important O- and C-glycosides.

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来源期刊

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.