5‐溴‐8‐硝基‐1‐萘酸在光信条件下作为醇类的保护基团

IF 2.7 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2025-09-23 DOI:10.1002/ejoc.202500574

Estela Sánchez‐Santos , Irene Boya del Teso , José J. Garrido‐González , Joaquín R. Morán , Ángel L. Fuentes de Arriba , Victoria Alcázar

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引用次数: 0

摘要

描述了使用易于获得的5 -溴- 8 -硝基- 1 -萘酸（NNapOH）作为伯醇和仲醇的保护基团。由于C‐1和C‐8萘取代基之间存在明显的位阻应变，保护基团可以在温和的还原条件下很容易地去除。该反应用不同的羟基底物进行了测试，包括单醇、1,2 -二醇和抗癌核糖核苷5 -氟吡啶。有趣的是，在线性1,2 -二醇的情况下，保护优先发生在仲醇上。此外，用N‐Boc羟基氨基酸衍生物进行了正交保护。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

5‐Bromo‐8‐Nitro‐1‐Naphthoic Acid as Protective Group for Alcohols Under Mitsunobu Conditions

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5‐Bromo‐8‐Nitro‐1‐Naphthoic Acid as Protective Group for Alcohols Under Mitsunobu Conditions

The use of the readily available 5‐bromo‐8‐nitro‐1‐naphthoic acid (NNapOH) as a protective group for primary and secondary alcohols is described. Protection is carried out under Mitsunobu conditions, and the protective group can be readily removed under mild reducing conditions, due to the significant steric strain between C‐1 and C‐8 naphthalene substituents. The reaction has been tested with different hydroxy substrates, including monoalcohols, 1,2‐diols, and the anticancer ribonucleoside 5‐fluorouridine. Interestingly, in the case of linear 1,2‐diols, protection occurs preferentially at the secondary alcohol. In addition, orthogonal protection is obtained with N‐Boc hydroxy amino acid derivatives.

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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.