Hydrochloric Acid → 9-[4-(Diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine

Participants

Reaction Steps

A solution of 2-[bis(t-butoxycarbonyl)amino]-9-[1-(t-butyldimethylsilyloxy)-4-(diethoxyphosphorylmethoxy)but-2-oxy]-6-methoxypurine (415 mg, 0.57 mmol) was dissolved in ethanol (5 ml) and 5M hydrochloric acid (0.6 ml) and heated under reflux for 3.5 h. The reaction was evaporated in vacuo and the residue chromatographed on silica, eluting with chloroform-methanol 10:1, affording 9-[4-(diethoxyphosphorylmethoxy)-1-hydroxybut-2-oxy]guanine (110 mg, 48%) as a pale tan solid. νmax (KBr) 3400, 1680, 1640 and 1600 cm-1 ; δH [(CD3)2SO] 1.22 (6H, t, J7.1 Hz, 2×CH2CH3), 1.91 (2H, m, CHCH2CH2O), 3.54 (2H, m, CH2OH), 3.74 (2H, m, CH2OCH2P), 3.85 (2H, d, J8.2 Hz, CH2P), 4.03 (4H, m, 2×CH2CH3), 4.30 (1H, m, HOCH2CH), 5.01 (1H, m, D2O exchangeable OH), 6.65 (2H, br.s, D2O exchangeable, NH2); m/z (FAB+ve Ion), 428 (MNa+), 406 (MH+).

Provenance & Evidence