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- “ For the deprotection of diethyl PMPA 5 with conc. HCl, we observe 10–16% acid catalyzed deamination of adenine to hypoxanthine ” . In Data not shown
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- Schultz , L. M. , Chapman , H. H. , Dupree , N. J. , Jones , R. J. , Kent , K. M. , Lee , T. T. , Louie , M. J. , Postich , M. J. , Prisbe , E. J. , Rohloff , J. C. and Yu , R. H. 1998 . Tetrahedron Lett. , 39 : 1853 – 1856 .
- Holy , A. and Rosenberg , I. 1987 . General procedure for cleavage of dialkyl phosphonates–preparation of 6: Diethyl PMEA 4 (9) (41.1 g, 0.125 mol) and chlorobenzene (0.125 L) were charged to a 1 L ACE™ glass pressure reactor containing a thermowell and a pressure gauge. The contents were stirred while TMSCl (56 mL, 0.44 mol) was added slowly. The reaction vessel was purged with N2, sealed, and heated to 125°C. The internal reactor pressure increased incrementally to a maximum of 30 psi after 9 h. The contents were cooled to r.t. at which time the pressure returned to ambient pressure and water (160 mL) was added with vigorous stirring. The layers were separated and the lower aqueous layer containing the product was collected. The aqueous layer was adjusted to pH = 3.2 with 25% NaOH (∼36 g), the resulting slurry cooled to 0°C and the solid collected by vacuum filtration. Water (40 mL) was added to the wet cake, the resulting slurry was heated to 70°C for 1 h, and then cooled to 0°C. The solid product was collected by vacuum filtration and dried under vacuum (50°C/28 mmHg) affording 33.0 g (0.120 mol, 96%) PMEA 6. NMR data for PMEA 6 was consistent with literature values . Collect. Czech. Chem. Commun. , 52 : 2801 – 2809 .
- In the same manner as above 48.3 g (0.140 mol) diethyl PMPA 5 (9) were deprotected with 4.5 equiv. TMSCl and yielded 30.3 g (0.105 mol, 75%) of PMPA 7 (99% pure by quantitative HPLC assay versus an external standard). 1H NMR (300 MHz, D2O, δ): 8.31 (s, 2H, Adenine–2H, –8H), 4.39 (dd, J = 14, 3 Hz, 1H, –CH 2N), 4.20 (dd, J = 14, 7 Hz, 1H, –CH 2N), 3.89 (m, 1H, –CH–), 3.58 (dd, J = 13, 9 Hz, 1H, –OCH 2P), 3.38 (dd, J = 13, 9 Hz, 1H, –OCH 2P), 1.07 (d, J = 6 Hz, 3H, –CH 3) 31P NMR (121 MHz, D2O, δ): 15.79
- Hampton , A. , Sasaki , T. and Paul , B. 1973 . J. Am. Chem. Soc. , 95 : 4404 – 4414 .