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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 6
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Articles

A novel synthesis of (2S)-3-(2,4,5-trifluorophenyl)propane-1,2-diol by sharpless asymmetric epoxidation method

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Pages 852-858 | Received 23 Oct 2018, Accepted 26 Jan 2019, Published online: 21 Feb 2019

References

  • (a) Lorand, K.; Ferenc, F. Synthesis of Carbocyclic and Heterocyclic β-aminocarboxylic Acids. Chem. Rev. 2014, 114, 1116-1169. DOI: 10.1021/cr300454h. (b) Tamas, A. M.; Ferenc, F. Peptidic Foldamers: Ramping Up Diversity. Chem. Soc. Rev. 2012, 41, 687-702. DOI: 10.1039/C1CS15097A. (c) Dan-Wei, Z.; Xin, Z.; Jun-Li, H.; Zhan-Ting, L. Aromatic Amide Foldamers: Structures, Properties, and Functions. Chem. Rev. 2012, 112, 5271-5316. DOI: 10.1021/cr300116k. (d) Chiara, C.; Tamas, A. M.; Oliver, R.; Lukasz, B. Peptides Containing β-amino Acid Patterns: Challenges and Successes in Medicinal Chemistry. J. Med. Chem. 2014, 57, 9718-9739. DOI: 10.1021/jm5010896.
  • (a) Juaristi, E.; Soloshonok, V. A. Enantioselective Synthesis of Beta-Amino Acids. John Wiley & Sons Press: New Jersey, 2005. (b) Masahiko, S.; Toshiaki, S.; Kazuo, M. Stereoselective Synthesis of β-Benzyl-α-alkyl-β-amino Acids from L-Aspartic Acid. J. Org. Chem. 2000, 65, 1298-1304. DOI: 10.1021/jo991241w.
  • (a) Greg, L. P. Sitagliptin: A Review of Its Use in Patients with Type 2 Diabetes Mellitus. Drugs. 2014, 74, 223-242. DOI: 10.1007/s40265-013-0169-1. (b) Dooseop, K.; Jennifer, E. K.; Scott, D. E.; Anthony, M.; Jinyou, X.; George, J. E.; Barbara, L.; Joseph K. W.; Kelly, A. D. P.; Reshma, A. P.; et al. Triazolopiperazine-amides as Dipeptidyl Peptidase IV Inhibitors: Close Analogs of JANUVIA™(Sitagliptin Phosphate). Biorg. Med. Chem. Lett. 2007, 17, 3373-3377. DOI: 10.1016/j.bmcl.2007.03.098. (c) Pablo, A.; Mark, S. K.; Jared, K. L.; Matilde, S.; Carolyn, M.; Debora, E. Effect of the dipeptidyl peptidase-4 inhibitor sitagliptin as monotherapy on glycemic control in patients with type 2 diabetes. Diabetes Care. 2006, 29, 2632-2637.
  • Sun, G. F.; Cai, Z. Y.; Zhou, W. C. Graphical Synthetic Routes of Sitagliptin. Chinese J. Pharm 2008, 39, 383-383.
  • (a) Chennam, S. S.; Wahajul, H. Efficient Stereocontrolled Synthesis of Sitagliptin Phosphate. Tetrahedron Asymmetry. 2014, 25, 1026-1030. DOI: 10.1016/j.tetasy.2014.06.001. (b) Li, L. Z.; Ying, J. D.; Gui, C. Z.; Hong, R. S.; Wen, H. H. A Practical Synthesis of Trifluorophenyl R-amino Acid: The Key Precursor for the New Anti-Diabetic Drug Sitagliptin. Chinese Chem. Lett. 2009, 20, 1397-1399. DOI: 10.1016/j.cclet.2009.06.036. (c) Gbor, T.; Eniko, F.; Ferenc, F. Improved Enzymatic Syntheses of Valuable β-arylalkyl-β-amino Acid Enantiomers. Org. Biomol. Chem. 2010, 8, 793-799. DOI: 10.1039/B920731G. (d) Karl, B. H.; Jaume, B.; Spencer, D.; Yi, H.; Michele, K.; Michael, P.; Nelo, R.; Dietrich, S.; Joseph, D. A.; David, A.; et al. First Generation Process for the Preparation of the DPP-IV Inhibitor Sitagliptin. J. Org. Proc. Res. Dev. 2005, 9, 634-639. DOI: 10.1021/op0500786. (e) Christopher, K. S.; Jacob, M. J.; Emily, C. M.; Jeffrey, C. M.; Sarena, T.; William, R. J.; Jeffrey, C. C.; Anke, K.; Fred, J. F.; Brands, J.; et al. Biocatalytic Asymmetric Synthesis of Chiral Amines from Ketones Applied to Sitagliptin Manufacture. Science. 2010, 329, 305-309.
  • (a) Derya, A.; Meryem, F.; Özlem, G.; Hasan, S.; Mehmet, F. S.; Ramazan, A.; Yunus, K. Novel and Stereospecific Synthesis of (2S)‐3‐(2,4,5‐Trifluorophenyl)propane‐1,2‐diol from D‐Mannitol. Helv. Chim. Acta. 2015, 98, 1127-1131. DOI: 10.1002/hlca.201500031. (b) Meryem, F.; Özlem, G.; Derya, A.; Hasan, S.; Mehmet, F. S.; Ramazan, A.; Yunus, K. Novel and Enantioselective Syntheses of (R)-and (S)-3-hydroxy-4-(2,4,5-trifluorophenyl) Butanoic Acid: A Synthon for Sitagliptin and Its Derivatives. Tetrahedron. 2012, 68, 2607-2610. DOI: 10.1016/j.tet.2012.01.095.
  • Zhonghua, P.; Xiaofeng, L.; von Geldern, T. W.; Kenton, L.; Daisy, P.; Kent, D. S.; Bradley, J. B.; Chunqiu, L.; Thomas, H. L.; Stephen, J. B.; et al. Discovery and Structure − Activity Relationships of Piperidinone- and Piperidine-Constrained Phenethylamines as Novel, Potent, and Selective Dipeptidyl Peptidase IV Inhibitors. J. Med. Chem. 2007, 50, 1983-1987. DOI: 10.1021/jm061436d.
  • (a) Sasikumar, M.; Milind, D. N. Simple and Efficient Synthesis of (S)-Dapoxetine. Synth. Commun. 2012, 42, 3061-3067. DOI: 10.1080/00397911.2011.575522. (b) Yun, G.; Robert, M. H.; Janice, M. K.; Soo, Y. K.; Hiroko, M.; Karl, B. S. Catalytic Asymmetric Epoxidation and Kinetic Resolution: Modified Procedures Including In Situ Derivatization. J. Am. Chem. Soc. 1987, 109, 5765-5780.
  • Steven, V. L.; Angus, J. P. S. L.; David, P.; Remedios, H. P.; Kevin, T. Hydrogenation of Aromatic Ketones, Aldehydes, and Epoxides with Hydrogen and Pd(0)EnCat™ 30NP. Beilstein. J. Org. Chem. 2006, 2, 15. DOI: 10.1186/1860-5397-2-15.

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