9-[1-(t-Butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]adenine → 9-[4-(Diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]adenine
Reaction equation
[Si]([O:8][CH2:9][CH:10]([O:23][N:24]1[CH:32]=[N:31][C:30]2[C:25]1=[N:26][CH:27]=[N:28][C:29]=2[NH2:33])[CH2:11][CH2:12][O:13][CH2:14][P:15]([O:20][CH2:21][CH3:22])([O:17][CH2:18][CH3:19])=[O:16])(C(C)(C)C)(C)C>C(O)(=O)C>[CH2:18]([O:17][P:15]([CH2:14][O:13][CH2:12][CH2:11][CH:10]([O:23][N:24]1[CH:32]=[N:31][C:30]2[C:25]1=[N:26][CH:27]=[N:28][C:29]=2[NH2:33])[CH2:9][OH:8])([O:20][CH2:21][CH3:22])=[O:16])[CH3:19]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]adenine (360 mg, 0.72 mmol) in 80% acetic acid (15 ml) was stirred at 85° C. for 3 h. The solvents were evaporated under vacuum and co-evaporated with toluene. The residue was chromatographed on silica, eluting with chloroform-methanol 10:1, affording 9-[4-(diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]adenine (220 mg, 79%) as a white solid, m.p. 86°-88° C. νmax (KBr) 3350, 3140, 1660, 1600 and 1540 cm-1 ; δH (CDCl3) 1.36 (6H, t, J6.8 Hz, 2×CH3CH2), 2.03 (1H, m, HOCH2CHCH2), 2.23 (1H, m, HOCH2CHCH2), 3.66 (2H, m, CH2OH)), 3.86 (4H, m, CH2OCH2P), 4.21 (4 H, m, 2×CH3CH2), 4.48 (1H, m, CHON), 5.32 (1H, br.s, D2O exchangeable, OH), 6.02 (2H, br.s, D2O exchangeable NH2), 8.24 (1H, s, H-2/H-8), 8.34 (1H, s, H-2/H-8). Found: C, 43.33; H, 6.27; N, 17.81%; M+ 389.1469. C14H24N5O6P requires C, 43.19; H, 6.21; N, 17.99%; M+ 389.1464.
Workup
- customThe solvents were evaporated under vacuum and co-evaporated with toluene
- customThe residue was chromatographed on silica
- washeluting with chloroform-methanol 10:1
Sources & evidence
- ORD record
- ord-6d1736f5a48345aabc6db6a4deb59c32
- Source dataset
- uspto-grants-1991_10
- Patent number
- US05055458
Reaction notes
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