1226
1H, H40), 6.12 (dd, J=6.4, 6.5, 1H, H10); C44H41O8N3P1S1, HR FAB MS [M−H]: 802.235. 50-O-DMT-Thymidine 30-O-(S-
phenyl methanephosphonothioate (7, B=Thy) was obtained from 50-O-DMT-thymidine (1 mmol). Yield 63% (FAST:SLOW
1
3:2). SLOW (RP). 31P NMR (CDCl3): 55.0, H NMR (CDCl3): 1.76 (d, J=15.6, 3H, P-CH3), 2.47 (m, 1H, H20), 2.71 (m,
1H, H200), 3.48 (m, 2H, H50, H500), 4.16 (m, 1H, H30), 5.43 (dd, J=5.8, 10.0, 1H, H40), 6.46 (dd, J=5.4, 9.0, 1H, H10);
C38H38O8N2P1S1, HR FAB MS [M−H]: 713.212, calcd 713.216. FAST (SP): 31P NMR (CDCl3): 54.73, 1H NMR (CDCl3):
1.72 (d, J=15.6, 3H, P-CH3), 2.54 (m, 2H, H20, H200), 3.49 (m, 2H, H50, H500), 4.34 (m, 1H, H30), 5.40 (m, 1H, H40), 6.43
(dd, J=5.6, 8.9, 1H, H10); C38H38O8N2P1S1, FAB MS [M−H]: 713.2. 50-O-DMT-N6-Benzoyl-20-deoxyadenosine 30-O-(S-
phenyl methanephosphonothioate) (7, B=ABz) was obtained from N6-benzoyl-20-deoxyadenosine (1 mmol). Yield 53%.
1
SLOW (RP): 31P NMR (CDCl3): 54.43, H NMR (CDCl3): 1.79 (d, J=15.6, 3H, P-CH3) 2.90 (m, 1H, H20), 3.12 (m, 1H,
H200), 3.5 (m, 2H, H50, H500), 4.35 (m, 1H, H40), 5.55 (m, 1H, H30), 6.53 (dd, 1H, J=5.5, 5.8, H10); C45H41O7N5P1S1, HR
FAB MS [M−H]: 826.234, calcd 827.237. FAST (SP): 31P NMR (CDCl3): 54.26, 1H NMR (CDCl3): 1.77 (d, J=15.5, 3H,
P-CH3), 2.69 (m, 1H, H20), 3.03 (m, 1H, H200), 3.6 (m, 2H, H50, H500), 4.54 (m, 1H, H30), 5.45 (m, 1H, H40), 6.52 (dd,
1H, J=5.4, 5.7, H10); C45H41O7N5P1S1, HR FAB MS [M−H]: 826.234. 50-O-DMT-N4-Isobutyryl-20-deoxyguanosine 30-O-
(S-phenyl methanephosphonothioate) (7, B=Gibu) was obtained from N4-isobutyryl-20-deoxyguanosine (1 mmol). Purified
by a column chromatography (twice) (CHCl3-3% EtOH), followed by precipitation from petroleum ether. Total yield: 57%.
1
SLOW (RP): 31P NMR (CDCl3): 55.00, H NMR (CDCl3): 1.76 (d, J=15.6, 3H, P-CH3), 2.80 (m, 2H, H20, H200), 3.25
(m, 1H, H500), 3.47 (dd, J=3.1, 10.6, 1H, H500), 4.16 (m, 1H, H40), 5.80 (m, 1H, H30), 6.14 (dd, J=5.9, 6.9, 1H, H10);
C42H43N5O8P1S1, HR FAB MS [M−H]: 808.253, calcd 808.257. FAST (SP): 31P NMR (CDCl3): 54.74, 1H NMR (CDCl3):
1.69 (d, J=15.2, 3H, P-CH3), 2.13 (m, 1H, H20), 2.55 (m, 1H, H200), 3.20 (dd, J=3.1, 10.7, 1H, H50), 3.42 (dd, 1H, J=2.9,
10.9, H500), 4.21 (m, 1H, H40), 6.76 (m, 2H, H30, H10); C42H43N5O8P1S1, HR FAB MS [M−H]: 808.253.
12. Wozniak, L. A.; Pyzowski, J.; Wieczorek, M.; Majzner, W.; Stec, W. J. J. Org. Chem. 1998, 61, 5395–5402.
13. Caruthers, M. H.; Haltiwanger, R. C. Acta Crystallogr. 1989, C45, 1639–1641.
14. (RP)-50-O-DMT-Thymidylyl-(30,50)-30-O-acetylthymidine 30-methanephosphonate (6) was obtained from (RP)-7 (B=Thy)
and 30-O-acetylthymidine. Reaction time 2 h; yield 42%; 31P NMR (CDCl3): 33.00 (89%), 34.55 (11%); 1H NMR (CDCl3):
1.58 (d, J=17.6, 3H, P-CH3); C44H48O14N4P1, FAB MS [M−H]: 887.3, calcd 887.87. (SP)-50-O-DMT-Thymidylyl-(30,50)-
30-O-acetylthymidine 30-methanephosphonate (6) was obtained from (SP)-7 (B=Thy) and 30-O-acetylthymidine. Reaction
time 2 h; yield 53%; 31P NMR (CDCl3): 33.05 (7%) 34.14 (93%); 1H NMR (CDCl3): 1.57 (d, J=17.6, 3H, P-CH3);
C44H48O14N4P1, FAB MS [M−H]: 887.3.
15. Lesnikowski, Z.; Zabawska, D.; Jaworska-Maslanka, M. M.; Schinazi, R. F.; Stec, W. J. New J. Chem. 1994, 18, 1197–1204.
16. Wozniak, L. A.; Chworos, A.; Pyzowski, J.; Stec, W. J. J. Org. Chem. 1998, 63, 9109–9112.