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Vol. 26 No. 9 (2014): Vol 26 Issue 9

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Synthesis and Crystal Structure of Monofluorinated Iminosugar Derivative (S)-1-((3R,4R,5S)-1-benzyl-4-fluoro-5-((4-nitrobenzoyl)oxy)piperidin-3-yl)ethane-1,2-diyl Bis(4-nitrobenzoate)

https://doi.org/10.14233/ajchem.2014.16492
Yi Yang
School of Chemistry and Pharmaceutical Engineering, Sichuan University of Science & 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 & 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 & 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 & Engineering, Zigong 643000, P.R. China
Yin-Ping Liu
School of Chemistry and Pharmaceutical Engineering, Sichuan University of Science & 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
Wei Yuan
School of Chemistry and Pharmaceutical Engineering, 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. 9 (2014): Vol 26 Issue 9

Abstract

Monofluorinated iminosugar derivative (S)-1-((3R,4R,5S)-1-benzyl-4-fluoro-5-((4-nitrobenzoyl)oxy)piperidin-3-yl)ethane-1,2-diyl bis(4-nitrobenzoate) (I) has been synthesized from triol (II) via ester formation. Compound (I) was fully characterized by IR, MS and 1H (13C, 19F) NMR spectra. In addition, the molecular structure of this compound was established by X-ray crystallography. The crystal of title compound crystallizes in monoclinic, spacegroup P21/n with a = 7.2630(14), b = 20.461(4), c = 11.456(2) Å, a = 90.00, b = 96.877(4), g = 90°, V = 1690.3(6) Å3, Z = 2, C35H29FN4O12, Mr = 716.62, Dc = 1.408 g/cm3, F(000) = 744 and μ(MoKa) = 0.111 mm-1. The final R = 0.0824 and wR = 0.2177 for 8897 observed reflections [I > 2s(I)] and R = 0.1333 and wR = 0.2497 for all data. From the analysis of the crystal structure, it was observed that the piperidinyl ring adopted the chair form conformation with the equatorial location of the large group. The identified distortions of conjugated systems, orthogonal multipolar interactions and p binding forces were also discussed through the analysis of electrostatic interactions at their origin.

Keywords

Iminosugar Piperidine Fluorine X-ray crystallography Electrostatic interactions
Yang, Y., Li, Y.-L., Cheng, C.-R., Deng, Z.-W., Liu, Y.-P., & Yuan, W. (2014). Synthesis and Crystal Structure of Monofluorinated Iminosugar Derivative (S)-1-((3R,4R,5S)-1-benzyl-4-fluoro-5-((4-nitrobenzoyl)oxy)piperidin-3-yl)ethane-1,2-diyl Bis(4-nitrobenzoate). Asian Journal of Chemistry, 26(9), 2748–2752. https://doi.org/10.14233/ajchem.2014.16492
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