对乙酰氧基碳酸酯在低聚糖合成中作为正交羟基保护基团的研究

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-07-02 DOI:10.1002/ejoc.202500311

Shih‐Yao Yen , Jiun‐Rung Guo , Yi‐Ling Yan , Yu‐Chen Chou , Ching‐Ching Yu , Chien‐Fu Liang

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引用次数: 0

摘要

介绍了对乙酰氧基碳酸苄基（ABC）在保护羟基功能方面的应用。这种羟基保护基团可以很容易地用廉价的市售4-羟基苄基醇作为原料制备。ABC基团可以在室温下通过三氟化镱催化酯交换选择性去除，而不影响常用的酸可切割保护基团，如叔丁基二甲基硅基（TBDMS）、对甲氧基苄基（PMB）、丙酮和苄基。值得注意的是，在低聚糖合成的糖基化条件下，ABC保护基团是稳定的。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

Insight on p‐Acetoxybenzyl Carbonate as an Orthogonal Hydroxyl Protecting Group in Oligosaccharide Synthesis

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Insight on p‐Acetoxybenzyl Carbonate as an Orthogonal Hydroxyl Protecting Group in Oligosaccharide Synthesis

This study describes the utility of p‐acetoxybenzyl carbonate (ABC) group for the protection of hydroxyl functions. This hydroxyl protecting group can be easily prepared using inexpensive commercially available 4‐hydroxybenzyl alcohol as the starting material. The ABC group can be selectively removed through ytterbium(III) triflate‐catalyzed transesterification at room temperature without affecting commonly used acid‐cleavable protecting groups, such as tert‐butyldimethylsilyl (TBDMS), p‐methoxybenzyl (PMB), acetonide, and benzylidenes. Notably, the ABC protecting group is stable under glycosylation conditions in oligosaccharide synthesis.

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

CiteScore

5.40

自引率

3.60%

发文量

752

审稿时长

1 months

期刊介绍： The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.