1. Hamilton, R., et al., The Reaction of Dimethyl Dioxirane with Diazomethylphosphonates - the First Synthesis of a Formylphosphonate Hydrate. Journal of the Chemical SocietyChemical Communications, 1994(1): p. 37-38.
2. Hamilton, R., et al., Reactions of diazomethylphosphonate: The first synthesis of a formylphosphonate hydrate. Phosphorus Sulfur and Silicon and the Related Elements, 1996. 109(1-4): p. 441-444.
3. Kolodiazhnyi, O.I., Asymmetric synthesis of hydroxyphosphonates. TetrahedronAsymmetry, 2005. 16(20): p. 3295-3340.
4. Dellaria, J.F., et al., New Inhibitors of Renin That Contain Novel Phosphostatine Leu-Val Replacements. Journal of Medicinal Chemistry, 1990. 33(2): p. 534-542.
5. Tao, M., et al., Novel peptidyl phosphorus derivatives as inhibitors of human calpain I. Journal of Medicinal Chemistry, 1998. 41(20): p. 3912-3916.
6. Stowasser, B., et al., New Hybrid Transition-State Analog Inhibitors of Hiv Protease with Peripheral C2-Symmetry. Tetrahedron Letters, 1992. 33(44): p. 6625-6628.
7. Snoeck, R., et al., Antivaccinia Activities of Acyclic Nucleoside Phosphonate Derivatives in Epithelial Cells and Organotypic Cultures. Antimicrobial Agents and Chemotherapy, 2002. 46: p. 3356-3361.
8. Peters, M.L., M. Leonard, and A.A. Licata, Role of alendronate and risedronate in preventing and treating osteoporosis. Cleveland Clinic Journal of Medicine, 2001. 68(11): p. 945-951.
9. Leder, B.Z. and H.M. Kronenberg, Gastroenterologists and choosing the right bisphosphonate. Gastroenterology, 2000. 119(3): p. 866-869.
10. Samanta, S. and C.G. Zhao, Organocatalytic enantioselective synthesis of alpha-hydroxy phosphonates. Journal of the American Chemical Society, 2006. 128(23): p. 7442-7443.
11. Dodda, R. and C.G. Zhao, Organocatalytic highly enantioselective synthesis of secondary alpha-hydroxyphosphonates. Organic Letters, 2006. 8(21): p. 4911-4914.
12. Dodda, R. and C.G. Zhao, Silver(I) triflate-catalyzed direct synthesis of N-PMP protected alpha-aminopropargylphosphonates from terminal alkynes. Organic Letters, 2007. 9(1): p. 165-167.
13. Dodda, R. and C.G. Zhao, Enantioselective synthesis of alphaaminopropargylphosphonates. Tetrahedron Letters, 2007. 48(25): p. 4339-4342.
14. Murray, R.W. and M. Singh, Organic Syntheses, Coll., 1998. 9: p. 5.
DEVELOPMENTS IN THE PREPARATION OF DIMETHYLDIOXIRANE DMD/DMDO
Year 2014,
Volume: 1 Issue: 3, 107 - 115, 01.06.2014
The synthesis of dimethyldioxirane DMD/DMDO is as complicated as its storage. It should be used within a week after its synthesis. Developments were gained in the synthetic procedure of DMD/DMDO in two steps and enough yield was obtained at moderate temperature compared to literature procedures -78 oC . The dry ice before trap was replaced with a condenser containing chilled methanol which also resulted the condensation of DMD/DMDO back from the vacuum trap. Diethyl formylphosphonate 6 was synthesized by the oxidation of diazomethylphosphonate 5 with DMD/DMDO at different temperatures starting from -78 ºC to 0 ºC
1. Hamilton, R., et al., The Reaction of Dimethyl Dioxirane with Diazomethylphosphonates - the First Synthesis of a Formylphosphonate Hydrate. Journal of the Chemical SocietyChemical Communications, 1994(1): p. 37-38.
2. Hamilton, R., et al., Reactions of diazomethylphosphonate: The first synthesis of a formylphosphonate hydrate. Phosphorus Sulfur and Silicon and the Related Elements, 1996. 109(1-4): p. 441-444.
3. Kolodiazhnyi, O.I., Asymmetric synthesis of hydroxyphosphonates. TetrahedronAsymmetry, 2005. 16(20): p. 3295-3340.
4. Dellaria, J.F., et al., New Inhibitors of Renin That Contain Novel Phosphostatine Leu-Val Replacements. Journal of Medicinal Chemistry, 1990. 33(2): p. 534-542.
5. Tao, M., et al., Novel peptidyl phosphorus derivatives as inhibitors of human calpain I. Journal of Medicinal Chemistry, 1998. 41(20): p. 3912-3916.
6. Stowasser, B., et al., New Hybrid Transition-State Analog Inhibitors of Hiv Protease with Peripheral C2-Symmetry. Tetrahedron Letters, 1992. 33(44): p. 6625-6628.
7. Snoeck, R., et al., Antivaccinia Activities of Acyclic Nucleoside Phosphonate Derivatives in Epithelial Cells and Organotypic Cultures. Antimicrobial Agents and Chemotherapy, 2002. 46: p. 3356-3361.
8. Peters, M.L., M. Leonard, and A.A. Licata, Role of alendronate and risedronate in preventing and treating osteoporosis. Cleveland Clinic Journal of Medicine, 2001. 68(11): p. 945-951.
9. Leder, B.Z. and H.M. Kronenberg, Gastroenterologists and choosing the right bisphosphonate. Gastroenterology, 2000. 119(3): p. 866-869.
10. Samanta, S. and C.G. Zhao, Organocatalytic enantioselective synthesis of alpha-hydroxy phosphonates. Journal of the American Chemical Society, 2006. 128(23): p. 7442-7443.
11. Dodda, R. and C.G. Zhao, Organocatalytic highly enantioselective synthesis of secondary alpha-hydroxyphosphonates. Organic Letters, 2006. 8(21): p. 4911-4914.
12. Dodda, R. and C.G. Zhao, Silver(I) triflate-catalyzed direct synthesis of N-PMP protected alpha-aminopropargylphosphonates from terminal alkynes. Organic Letters, 2007. 9(1): p. 165-167.
13. Dodda, R. and C.G. Zhao, Enantioselective synthesis of alphaaminopropargylphosphonates. Tetrahedron Letters, 2007. 48(25): p. 4339-4342.
14. Murray, R.W. and M. Singh, Organic Syntheses, Coll., 1998. 9: p. 5.
Ayhan Sıtkı Demir
This is me
Department of Chemistry, Middle East Technical University, Ankara, 06531 Turkey
İlke Şimşek
This is me
Department of Chemistry, Middle East Technical University, Ankara, 06531 Turkey
Muhammad Raza Shah
This is me
International Center for Chemical and Biological Sciences, HEJ Research Institute of Chemistry, University of Karachi, Karachi-75270, Pakistan