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Vol. 26 No. 10 (2014): Vol 26 Issue 10

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Synthesis, Characterization and X-ray Crystal Structure of 2',3'-Dideoxy-6'-fluorocarbocyclic Nucleoside Analogue

https://doi.org/10.14233/ajchem.2014.16746
Yi Yang
School of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, Zigong 643000, P.R. China ;Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, Sichuan University of Science & Engineering, Zigong 643000, P.R. China
Yu-Long Li
School of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, Zigong 643000, P.R. China ;Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, Sichuan University of Science & Engineering, Zigong 643000, P.R. China
Yan Jiang
School of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, Zigong 643000, P.R. China ;Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, Sichuan University of Science & Engineering, Zigong 643000, P.R. China
Jian-Zhang Li
School of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, Zigong 643000, P.R. China ;Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, Sichuan University of Science & Engineering, Zigong 643000, P.R. China
Zhi-Wen Deng
School of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, Zigong 643000, P.R. China ;Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, Sichuan University of Science & Engineering, Zigong 643000, P.R. China
Chun-Ru Cheng
School of Chemistry and Pharmaceutical Engineering, Sichuan University of Science and Engineering, Zigong 643000, P.R. China ;Key Laboratory of Green Catalysis of Higher Education Institutes of Sichuan, Sichuan University of Science & Engineering, Zigong 643000, P.R. China

Corresponding Author(s) : Yi Yang

yangyiyoung@163.com

Asian Journal of Chemistry, Vol. 26 No. 10 (2014): Vol 26 Issue 10

Abstract

A novel 2',3'-dideoxy-6'-fluorocarbocyclic nucleoside analogue (1) has been synthesized via the critical Mitsunobu reaction of a-fluoroalcohol (2) with 6-chloropurine in the presence of triphenylphosphine and diethyl azodicarboxylate. Nucleoside analogue (1) was fully characterized by IR, 1H (19F, 13C) NMR and MS spectroscopy. In addition, the molecular structure of nucleoside analogue 1 was established by X-ray crystallography. The crystal of compound 1 crystallizes in monoclinic, space group Pna21 with a = 6.2705(7), b = 7.9183(8), c = 24.348(2) Å, V = 1204.3(2) Å3, Z = 2, C26H26N5O2F, Mr = 459.52, Dc = 1.267 g/cm3, F(000) = 484. The final R = 0.0376 and wR = 0.0777 for 6645 observed reflections with I > 2s(I) and R = 0.0542 and wR = 0.0827 for all data. From the analysis of the crystal structure, it was found that C(1)-F(1)···H(7B)-C(7)sp3 contacted in a distance of 2.655 Å in spite of the fact that the C-F was a poor hydrogen-bond acceptor. Moreover, the short contact also existed in N(2)···H(3)-C(3)sp2 with the length of 2.726 Å in which C(3)sp2-H(3) worked as an unusual hydrogen-bond donor, which showed significant difference from the traditional N···H-X hydrogen-bond interaction.

Keywords

Fluorine Carbocyclic nucleoside Crystal structure Hydrogen bond Electrostatic interaction
Yang, Y., Li, Y.-L., Jiang, Y., Li, J.-Z., Deng, Z.-W., & Cheng, C.-R. (2014). Synthesis, Characterization and X-ray Crystal Structure of 2’,3’-Dideoxy-6’-fluorocarbocyclic Nucleoside Analogue. Asian Journal of Chemistry, 26(10), 3077–3081. https://doi.org/10.14233/ajchem.2014.16746
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