Dapagliflozin Synthesis Route

Dapagliflozin Synthesis

Dapagliflozin (Synonyms: (1S)-1,5-Anhydro-1-C-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-D-glucitol)

Dapagliflozin is an inhibitor of sodium-glucose transporter 2 (SGLT2; IC50s = 1.12 and 3 nM for the human and rat enzymes, respectively).1 It is selective for SGLT2 over SGLT1 (IC50s = 1,391 and 620 nM for the human and rat enzymes, respectively) and human adipocyte glucose transporter (GLUT) activity at 20 µM. Dapagliflozin (0.1 and 1 mg/kg) increases urinary glucose levels in normal and Zucker diabetic rats. It decreases fasting and fed plasma glucose levels in Zucker diabetic rats when administered at doses of 0.01, 0.1, and 1 mg/kg.

Dapagliflozin

An SGLT2 inhibitor

Item No. AB52027
CAS No. 461432-26-8
Purity: 98%

50mg

＄12.00

＄73.00

＄232.00

10g

＄423.00

25g

＄717.00

100g

＄1,837.00

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Dapagliflozin Synthetic Route

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1.1: oxalyl dichloride; N,N-dimethyl-formamide / dichloromethane / 10 h / 20 °C
2.1: Aluminum Chloride / dichloromethane / 1 h / -5 - 20 °C / Inert atmosphere
2.2: 2 h / -5 - 0 °C / Inert atmosphere
3.1: Aluminum Chloride; sodium tetrahydridoborate / tetrahydrofuran / 18 h / 5 - 20 °C / Inert atmosphere
4.1: BBr3 / dichloromethane / -10 - 0 °C / Inert atmosphere
5.1: triethylamine / acetonitrile / 2 h / 5 - 15 °C
6.1: 4-methyl-morpholine / tetrahydrofuran / 5 - 25 °C / Inert atmosphere
7.1: n-butyllithium / tetrahydrofuran; hexane; toluene / 0.5 h / -65 °C / Inert atmosphere
7.2: 3 h / -65 - -55 °C
7.3: 16 h / 20 - 25 °C
8.1: triethylsilane; boron trifluoride diethyl ether complex / dichloromethane; acetonitrile / 2 h / -30 - -10 °C / Inert atmosphere
9.1: Cs2CO3; N,N,N-tributyl-1-butanaminium iodide / N,N-dimethyl-formamide / 12 h / 40 °C / Inert atmosphere

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References

1.J.Med. Chem. 2014, 57, 1236−1251. 
2.Han, S., Hagan, D.L., Taylor, J.R., et al. Dapagliflozin, a selective SGLT2 inhibitor, improves glucose homeostasis in normal and diabetic rats. Diabetes 57(6), 1723-1729 (2008).