Expanding the Scope of a One-Pot Double Displacement Protocol to Access the All-Rare-Sugar-Containing Trisaccharide Unit of Pseudomonas stutzeri OX1

IF 4.9 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2024-11-12 DOI:10.1021/acs.orglett.4c03788

Amar K. Mishra, Balasaheb K. Ghotekar, Chanchal K. Puley, Suvarn S. Kulkarni

引用次数: 0

Abstract

Herein, we have explored a one-pot bis-triflation and regioselective displacement protocol with d-fucose 2,4-diol to access various rare 6-deoxy amino d-sugars. This strategy enabled the first total synthesis of the trisaccharide unit of Pseudomonas stutzeri OX1 strain containing d-perosamine and d-tomosamine. Installation of a 1,2-cis linkage and late-stage N-formylation are the key challenges in the total synthesis, which was accomplished via the longest linear sequence of 21 steps with 1.2% overall yield.

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扩大一锅双置换方案的范围，以获得含有全稀有糖的盐假单胞菌 OX1 三糖单元

在此，我们探索了一种与 d-岩藻糖 2,4-二醇进行双三叉化和区域选择性置换的一锅式方案，以获得各种稀有的 6-脱氧氨基 d-糖。这一策略首次实现了含有 d-perosamine 和 d-tomosamine 的假单胞菌 OX1 菌株三糖单元的全合成。安装 1,2-顺式连接和晚期 N-酰化是全合成的关键挑战，通过 21 个步骤的最长线性序列完成了全合成，总产率为 1.2%。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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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.