Acid-Catalyzed Transformation of Pyranosides into Furanosides as a Tool for Preparation of Furanoside Synthetic Blocks,Organic Letters

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Acid-Catalyzed Transformation of Pyranosides into Furanosides as a Tool for Preparation of Furanoside Synthetic Blocks
Organic Letters ( IF 4.9 ) Pub Date : 2024-09-13 , DOI: 10.1021/acs.orglett.4c02984
Dmitry A Argunov ₁ , Uliana S Aladysheva ₁ , Vadim B Krylov _{1,

2} , Nikolay E Nifantiev ₁

Affiliation

The importance of natural glycoconjugates containing furanoside residues causes a continued demand for the development of efficient methods for the synthesis of corresponding oligosaccharide derivatives to be used as molecular probes in glycobiological studies. Currently, the chemical synthesis of furanose-containing oligosaccharides often represents a significant challenge because of the lack of short, efficient, and reliable methods for the preparation of selectively substituted furanoside blocks. Herein, we report an easy protocol toward galactofuranose-containing molecules based on the unusual equilibrium between pyranoside and furanoside forms observed for a series of substituted galactosides. The method’s utility is illustrated by the syntheses of furanoside-containing oligosaccharides related to the antigenic polysaccharides of Aspergillus fumigatus and Klebsiella pneumoniae O2ac.

中文翻译：

酸催化吡喃糖苷转化为呋喃糖苷作为制备呋喃糖苷合成嵌段的工具

含有呋喃糖苷残基的天然糖缀合物的重要性引起了对开发有效方法的持续需求，该方法用于合成相应的寡糖衍生物，以用作糖生物学研究中的分子探针。目前，由于缺乏用于制备选择性取代的呋喃糖苷嵌段的简短、有效和可靠的方法，含呋喃糖寡糖的化学合成通常是一个重大挑战。在此，我们报告了一种基于呋喃半乳糖分子的简单方案，该方案基于在一系列取代的半乳糖苷中观察到的吡喃糖苷和呋喃糖苷形式之间的不寻常平衡。该方法的实用性通过与烟曲霉和肺炎克雷伯菌O2ac的抗原多糖相关的含呋喃糖苷寡糖的合成来说明。

更新日期：2024-09-13

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