Selective Methylation of Nucleosides via an In Situ Generated Methyl Oxonium,The Journal of Organic Chemistry

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Selective Methylation of Nucleosides via an In Situ Generated Methyl Oxonium
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-02-15 , DOI: 10.1021/acs.joc.3c02578
Xiao-Yang Jin ₁ , Yin-Ming He _{1,

2} , Tian-He Hui _{1,

2,

3} , Li Liu _{1,

2} , Liang Cheng _{1,

2,

3}

Affiliation

A very mild and efficient procedure has been developed for the preparation of N-methylated uridine, pseudouridine, guanosine and inosine derivatives. This process was compatible with free hydroxyls within the ribose and did not require precautions on the protection or deprotection of other functionalities. The key to this extremely mild methylation without protection relied on the in situ generated methyl oxonium from the Wittig reagent and methanol. A putative mechanism for the selective methylation was also proposed.

中文翻译：

通过原位生成的甲基氧鎓选择性甲基化核苷

已经开发出一种非常温和且有效的方法用于制备N-甲基化尿苷、假尿苷、鸟苷和肌苷衍生物。该过程与核糖内的游离羟基相容，并且不需要对其他功能性的保护或脱保护采取预防措施。这种无保护的极其温和的甲基化的关键依赖于维蒂希试剂和甲醇原位生成的甲基氧鎓。还提出了选择性甲基化的假定机制。

更新日期：2024-02-15

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