Citation: ZHANG Ling-Yu, XU Hua-Qiang, SHI Yong-Heng, WANG Yu-Li, WANG Jian-Wu, ZHAO Gui-Long. Synthesis and Crystal Structure of Tianagliflozin Triacetate[J]. Chinese Journal of Structural Chemistry, ;2014, 33(1): 85-89. shu

Synthesis and Crystal Structure of Tianagliflozin Triacetate

1.
a School of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, China;
2.
b Tianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, China

Received Date: 14 May 2013
Available Online: 11 November 2013
Fund Project: Supported by Natural Science Foundation of China (21302141) (21302141)

The title compound tianagliflozin triacetate 1 was synthesized and its crystal structure was determined by single-crystal X-ray diffraction. The crystal belongs to monoclinic system (C₂₇H₃₁ClO₈, M_r=518.97), space group P2₁ with a=5.3913(11), b=16.137(2), c=15.411(3) Å, β=94.15(3)°, V=1337.3(5) Å³, Z=2, D_c=1.289 g/cm³, F(000)=548, μ=0.190 mm^-1, the final R=0.0374 and wR=0.0809 for 3981 observed reflections (I>2σ(I)). The structure of 1, triacetate of a highly potent SGLT2 inhibitor tianagliflozin, was unambiguously determined by single-crystal X-ray diffraction, which helped to confirm the desired β configuration at the anomeric center and the position where the deoxylation occurred. The two benzene rings in the lattice are basically orthogonal to each other. There are four intermolecular hydrogen bonds in the crystal, which helps to further stabilize the crystal.
- crystal structure,
- anti-diabetic drug,
- SGLT2 inhibitor,
- synthesis,
- tianagliflozin
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