反应详情

温度

0 °C

To a stirred solution of 3'-O-(t-butyldiphenylsilyl)-5'-O-phthalimidothymidine (10 g, 16 mmol) in dry CH2Cl2 (100 ml) was added methylhydrazine (1.3 ml, 24 mmol) under argon at room temperature and solution stirred for 12 h. The solution was cooled (0 °C.) and filtered. The white residue was washed with CH2Cl2 (2×25 ml) and combined filtrates were evaporated to furnish gummy residue. The residue on purification by silica gel column chromatography (elution with CH2Cl2 :MeOH, 98:2, v/v) furnished 7.03 g (89%) of 5'-O-amino-3'-O-(t-butyldiphenylsilyl)thymidine that crystallized from CH2Cl2 /MeOH mp 141°-143° C. 1H NMR (DMSO-d6) δ11.29 (s, 1, NH), 7.42-7.62 (m, 11, TBDPhH, C6H), 6.25 (dd, 1, H1', J1',2' =8.4 Hz, J1',2" =6.3 Hz), 6.02 (s, 2, NH2), 4.35 (m, 1, H4'), 4.04 (m, 1, H3'), 3.34-3.51 (m, 2, H5',5"), 2.04 (m, 2, H2',2"), 1.73 (s, 3, CH3), 1.03) (s, 9, C(CH3)3). Anal. Calcd. for C26H33O5N3Si: C, 63.00; H, 6.71; N, 8.48. Found: C, 62.85; H, 6.67; N, 8.32.

1. filtrationfiltered
2. washThe white residue was washed with CH2Cl2 (2×25 ml)
3. customwere evaporated
4. customto furnish gummy residue
5. customThe residue on purification by silica gel column chromatography (
6. washelution with CH2Cl2