7481-86-9Relevant academic research and scientific papers
Study on disulfur-backboned nucleic acids: Part 3. Efficient synthesis of 3′,5′-dithio-2′-deoxyuridine and deoxycytidine
Shang, Peihua,Wang, Hua,Cheng, Changmei,Zheng, Hongchao,Zhao, Yufen
experimental part, p. 1272 - 1281 (2009/04/11)
A general method is described for synthesizing 3′,5′-dithio- 2′-deoxypyrimidine nucleosides 6 and 13 from normal 2′- deoxynucleosides. 2,3′-Anhydronucleosides 2 and 9 are applied as intermediates in the process to reverse the conformation of 3′-position on sugar rings. The intramolecular rings of 2,3′-anhydrothymidine and uridine are opened by thioacetic acid directly to produce 3′-S-acetyl- 3′-thio-2′-deoxynucleosides 3 or 5. To cytidine, OH- ion exchange resin was used to open the ring and 2′-deoxycytidine 10 was abtained in which 3′-OH group is in threo-conformation. The 3′-OH is activated by MsCl, and then substituted by potassium thioacetate to form the S,S′-diacetyl-3′,5′-dithio-2′-deoxycytidine 12. The acetyl groups in 3′,5′ position are removed rapidly by EtSNa in EtSH solution to afford the target molecules 6 and 13. The differences of synthetic routes between uridine and cytidine are also discusssed. Copyright Taylor & Francis Group, LLC.
