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| New Synthetic Route of Novel SGLT2 Inhibitor——3-Oxodapagliflozin |
| JIANG Lin-lin1, YIN Ling1, XU Wei-ren2, TANG Li-da2, WANG Wen-jin2, ZHAO Gui-long2 |
| 1. Department of Chemistry and Chemical Engineering, Jining University, Qufu 273155, China; 2. Tianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, China |
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Abstract The key intermediate——2,4,6-tri-O-benzyl-3-oxo-D-gluconolactone ethylene dithioketal(10), was prepared by nine step reaction from 4-methoxyphenyl-β-D-glucopyranoside. Methyl 2,4,6-tri-O-benzyl-1-［4-chloro-3-(4-ethoxybenzyl)phenyl］-3-oxo-α/β-D-glucopyranoside ethylene dithioketal(12) was synthesized by nucleophilic addition of 10 with 5-bromo-2-chloro-4′-ethoxybiphenyl. The novel SGLT2 inhibitor, 3-oxodapagliflozin, was synthesized by reduction and deprotection from 12. The overall yield was 9%. Eleven novel compounds were involved in the synthetic route. The structures were characterized by 1H NMR， 13C NMR， IR and HR-ESI-MS.
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Received: 23 December 2014
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2015, Vol. 23 
