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An Improved Approach for Practical Synthesis of 5-Hydroxymethyl-2'-deoxycytidine (5hmdC) Phosphoramidite and Triphosphate. 2022

Dong-Zhao Yang, and Zhen-Zhen Chen, and Mei Chi, and Ying-Ying Dong, and Shou-Zhi Pu, and Qi Sun
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University, Nanchang 330013, China.

5-Hydroxymethyl-2'-deoxycytidine (5hmdC) phosphoramidite and triphosphate are important building blocks in 5hmdC-containing DNA synthesis for epigenetic studies. However, efficient and practical methods for the synthesis of these compounds are still limited. The current research provides an intensively improved synthetic method that enables the preparation of commercially available cyanoethyl-protected 5hmdC phosphoramidite with an overall yield of 39% on 5 g scale. On the basis of facile and efficient accesses to cyanoethyl protected-5hmdU and 5hmdC intermediates, two efficient synthetic routes for 5hmdC triphosphate were also developed.

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