A simple, rapid and efficient protocol for the selective phosphorylation of phenols with dibenzyl phosphite

Tetrahedron Letters

Volumn 37, Issue 6, 1996, Pages 771-774

  Silverberg, Lee J ^a   Dillon, John L ^a   Vemishetti, Purushotham ^a  

^a BRISTOL MYERS SQUIBB COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ORGANOPHOSPHORUS COMPOUND; PHENOL DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PHOSPHORYLATION; REACTION ANALYSIS; TECHNIQUE;

EID: 0030047044     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02294-5     Document Type: Article

References (34)

1. Abstracted in part from Silverberg, L.J.; Vemishetti, P.; Dillon, J.L.; Usher, J.J. U.S. Pat. 5,459,248.
2. a) Atherton, F.R.; Openshaw, H.T.; Todd, A.R. J. Chem. Soc. 1945, 382-5.
3. b) Fieser, L.F.; Fieser, M. Reagents for Organic Synthesis Vol. I; John Wiley and Sons: New York. 1967; pp. 198-9.
4. a) All experiments reported herein were performed with 2 (technical grade) from Aldrich Chemical Co.
5. b) Friedman, O.M.; Klass, D.L.; Seligman, A.M. J. Am. Chem. Soc., 1954, 916-7.
6. a) Atherton, F.R.; Todd, A.R. J. Chem. Soc. 1947, 674-8.
7. b) Atherton, F.R.; Openshaw, H.T.; Todd, A.R. J. Chem. Soc. 1945, 660-3.
8. a) Steinberg, G.M. J. Org. Chem. 1950, 15, 637-47.
9. b) Steinberg, G.M. U.S. Pat. 2,666,778.
10. Kenner, G.W.; Williams, N.R. J. Chem. Soc. 1955, 522.
11. Zwierzak, A. Synthesis 1976, 305.
12. a) Purnanand; Batra, B.S.; Pant, B.P. Tetrahedron Lett. 1989, 30, 1687-8.
13. b) Batra, B.S.; Purnanand Ind. J. Chem. 1991, 30B, 57.
14. Oza, V. ; Corcoran, R.C. Organic Abstract #493, 207th ACS National Meeting, March 13-17, 1994.
15. Stowell, J.K.; Widlanski, T.S. Tetrahedron Lett., 1995, 36, 1825-6.
16. a) Saulnier, M.G.; Senter, P.D.; Kadow, J.F. U.S. Pat. 4,904,768.
17. b) Drugs of the Future 1992, 17, 779-81.
18. c) Favreau, D. Eur. Pat. 53755-A1.
19. a) von Kuhn, M.; Keller-Juslen, C.; von Wartburg, A. Helv. Chim. Acta 1969, 52, 944-7.
20. b) 3 was purchased from Good Land Enterprises Ltd., 3213 Coleridge Ave., Vancouver, B.C., Canada V5S 3A6.
21. a) Saulnier, M.G.; Kadow, J.F.; Langley, D.R.; Tun, M.M. Eur. Pat. 511563-A1.
22. b) Saulnier, M.G.; Langley, D.R.; Kadow, J.F.; Senter, P.D.; Knipe, J.O. Bio. Med. Chem. Lett. 1994, 4, 2567.
23. a) Veeneman, G.H.; Broxterman, H.J.G.; van der Marel, G.A.; van Boom, J.H. Tetrahedron Lett. 1991 32, 6175-8.
24. b) Yu, K.L; Fraser-Reid, B. Tetrahedron Lett. 1988, 29, 979-82.
25. a) Rao, V.S.; Perlin, A.S. Carbohydr. Res. 1980, 83, 175.
26. b) Bajwa, J.S. Tetrahedron Lett. 1992, 33, 2299.
27. Hofle, G.; Steglich, W.; Vorbruggen, H. Ang. Chem. Int. Ed. Eng. 1978, 17, 569-83.
28. 2P(O)I: Stromberg, R.; Stawinski, J. Nuc. & Nuc. 1987, 6, 815-20.
29. 2P(O)F: Watanabe, Y.; Hyodo, N.; Ozaki, S. Tetrahedron Lett., 1988, 29, 5763.
30. 13C NMR, MS, and TLC or HPLC. Additional data for solid products are given in the footnotes below.
31. Kenner, G.W.; Mather, J. J. Chem. Soc. 1956, 3524.
32. Light orange solid. M.P.: 67.5-72°C.
33. White solid. Elemental Analysis: Calc.C, 63.64; H, 5.04. Found C, 63.84; H, 4.98. M.P. 207°C (DSC).
34. White solid. M.P. 198°C (decomposition) (DSC).