HCID 19993533, compound → HCID 19993505, compound

Participants

Reaction Steps

A solution of 2-[bis(t-butoxycarbonyl)amino]-9-[2-(t-butyldimethylsilyloxy)-3-(diethoxyphosphorylmethoxy) propoxy]-6-methoxypurine (0.66 g, 0.91 mmol) in 80% acetic acid (25 ml) was stirred at 85° C. for 4 h. The solution was evaporated in vacuo and the residue chromatographed on silica, eluting with chloroformmethanol 25:1, affording 2-amino-9-[3-(diethoxyphosphorylmethoxy)-2-hydroxypropoxy)-6-methoxypurine (275mg, 75%) as a clear gum. νmax (film) 3460, 3340, 1640, 1580, 1460 and 1390 cm-1 ; δH (CDCl3) 1.34 (6H, t, J6.9 Hz, 2×CH3CH2), 3.75 (2H, m, CH2OCH2P), 3 89 (2H, d, J7.7 Hz, CH2P), 4.04 (1H, m, CHOH), 4.09 (3H, s, OCH3), 4.17 (4H, m, 2×CH3CH 2), 4.34 (2H, m, CH2ON), 5.09 (2H, br.s, D2O exchangeable, NH2), 7.78 (1H, s, H-8). Found: C, 40.67; H, 6.18, N, 16.54%; M+ 405.1413. C14H24N5O7P.0.5H2O requires C, 40.58; H, 6.08; N, 16.90%; M+ 405.1413.

Provenance & Evidence