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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 23
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ARTICLES

Facile and green synthesis of dapagliflozin

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Pages 3373-3379 | Received 24 Jul 2019, Published online: 20 Sep 2019

References

  • Wu, Q. P.; Simons, C. Synthetic Methodologies for C-Nucleosides. Synthesis 2004, 10, 1533–1553. DOI: 10.1055/s-2004-829106.
  • Lee, D. Y. W.; He, M. S. Recent Advances in Aryl C-Glycoside Synthesis. Curr. Top. Med. Chem. 2005, 5, 1333–1350. DOI: 10.2174/156802605774643042.
  • (a) Lemaire, S.; Houpis, L. N.; Xiao, T. T.; Li, J. J.; Digard, E.; Gozlan, C.; Liu, R. M.; Gavryushin, A.; Diène, C.; Wang, Y. C.; et al. Stereoselective C-Glycosylation Reactions with Arylzinc Reagents. Org. Lett. 2012, 14, 1480–1483. DOI: 10.1021/ol300220p.; (b) Anna, S.; Gerald, K.; Marie, A.; Johan, W.; Helena-Peilot, S.; Cecilia, K.; Laurent, K.; Ryan, G. Chem. Eur. J. 2018, 24, 2832–2836.
  • Kraus, G. A.; Molina, M. T. A Direct Synthesis of C-Glycosyl Compounds. J. Org. Chem. 1988, 53, 752–753. DOI: 10.1021/jo00239a009.
  • Streicher, H.; Reine, M.; Schmidt, R. R. Synthesis and Reactions of C-Hetaryl Substituted Ketoses. J. Carbohydr. Chem. 1997, 16, 277–298. DOI: 10.1080/07328309708006530.
  • Thirumala, R. S.; Sajja, E. Process for the preparation of (1s)-1,5-anhydro-1-c-[4-chloro-3-[(4-ethoxyphenyl)methyl]phenyl]-d-glucitol and its solvate thereof. WO2015132803 A2, September 11, 2015.
  • Liou, J.; Wu, Y. L.; Li, S. B.; Xu, G. Processes for the preparation of sglt2 inhibitors. WO2010022313 A2, February 25, 2010.
  • (a) Henschke, J. P.; Lin, C. W.; Wu, P. Y.; Hsiao, C. N.; Liao, J. H.; Hsiao, T. Y. Process for the preparation of β-c-aryl glucosides. WO2013068850 A2, May 16, 2013.; (b) Hsiao, T.-Y.; Liao, J.-H. Process for preparing aryl C-glucosides as SGLT2 inhibitors and intermediates thereof. US20170240520 A1, August 24, 2017.
  • Lin, T. S.; Li, Y. W.; Song, J. S.; Hsieh, T. C.; Yeh, H. W.; Hsu, L. C.; Lin, C. J.; Wu, S. H.; Liang, P. H. Synthesis and Biological Evaluation of Novel C-Aryl d-Glucofuranosides as Sodium-Dependent Glucose co-Transporter 2 Inhibitors. Bioorg. Med. Chem. 2013, 21, 6282–6291. DOI: 10.1016/j.bmc.2013.08.067.
  • Yusuke, I.; Noriko, N.; Harumi, T.; Ikuyo, T.; Kazuo, U. Silica-Supported Heteropoly Acid Catalyst for Liquid-Phase Friedel–Crafts Reactions. Bull. Chem. Soc. Jpn. 1989, 62, 2159–2162.
  • Chiche, B.; Finiels, A.; Gauthier, G.; Geneste, P.; Graille, J.; Pioch, D. Friedel-Crafts Acylation of Toluene and p-Xylene with Carboxylic Acids Catalyzed by Zeolites. J. Org. Chem. 1986, 51, 2128–2130. DOI: 10.1021/jo00361a039.
  • Wang, Q. L.; Ma, Y. D.; Ji, X. D.; Yan, H.; Qiu, Q. Regioselective Acylation of Anisole with Carboxylic Acids Over HZSM-5 Catalyst. J. Chem. Soc. Chem. Commun. 1995, 22, 2307–2308. DOI: 10.1039/c39950002307.
  • Sarvari, M. H.; Sharghi, H. Simple and Improved Procedure for the Regioselective Acylation of Aromatic Ethers with Carboxylic Acids on the Surface of Graphite in the Presence of Methanesulfonic Acid. Synthesis 2004, 13, 2165–2168. DOI: 10.1055/s-2004-831162.
  • Sarvari, M. H.; Sharghi, H. Solvent-Free Catalytic Friedel-Crafts Acylation of Aromatic Compounds with Carboxylic Acids by Using a Novel Heterogeneous Catalyst System:p-Toluenesulfonic Acid/Graphite. HELVETICA. 2005, 88, 2282–2287. DOI: 10.1002/hlca.200590162.
  • Wilkinson, M. C. “Greener” Friedel-Crafts Acylations: A Metal- and Halogen-Free Methodology. Org. Lett. 2011, 13, 2232–2235. DOI: 10.1021/ol200482s.
  • Wilkinson, M. C.; Saez, F.; Hon, W. L. Application of the Catalytic Friedel-Crafts Acylation Reaction and Regioselectivity Correlations. Synlett. 2006, 7, 1063–1066. DOI: 10.1055/s-2006-939705.
  • Liu, G. C.; Xu, B. Hydrogen Bond Donor Solvents Enabled Metal and Halogen-Free Friedel–Crafts Acylations with Virtually No Waste Stream. Tetrahedron Lett. 2018, 59, 869–872. DOI: 10.1016/j.tetlet.2018.01.026.
  • Kakinuma, H.; Oi, T.; Hashimoto-Tsuchiya, Y.; Arai, M.; Kawakita, Y.; Fukasawa, Y.; Iida, I.; Hagima, N.; Takeuchi, H.; Chino, Y.; et al. (1 S )-1,5-Anhydro-1-[5-(4-Ethoxybenzyl)-2-Methoxy-4-Methylphenyl]-1-Thio- d -Glucitol (TS-071) Is a Potent, Selective Sodium-Dependent Glucose Cotransporter 2 (SGLT2) Inhibitor for Type 2 Diabetes Treatment. J. Med. Chem. 2010, 53, 3247–3261. DOI: 10.1021/jm901893x.

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