Synthesis and Crystal Structure of Tianagliflozin Triacetate

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,Mr = 518.97),space group P21 with a = 5.3913(11),b = 16.137(2),c = 15.411(3) ,β = 94.15(3)°,V = 1337.3(5) 3,Z = 2,Dc = 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.     

3,6-二脱氧达格列净的合成及其降血糖活性研究

利用达格列净作为原料经过两条路线合成了3,6-二脱氧达格列净,其3,6-二脱氧的位置进一步经过了NOE技术确认,体外h SGLT2抑制试验和大鼠尿糖排泄试验表明,所合成的3,6-二脱氧达格列净几乎没有SGLT2抑制活性,说明SGLT2抑制剂结构中葡萄糖片段上3-OH和6-OH同时脱除会导致SGLT2抑制剂完全丧失活性。