TBAF tetrahydrofuran → 3'-o-Aminothymidine

Participants

Reaction Steps

3'-O-Amino-(t-butyldimethylsilyl)thymidine was deblocked with (Bu)4NF/THF in standard way to furnish compound 4 (72%). Crystallized from ether/hexanes/ethanol as fine needles, mp 81° C. 1H NMR (Me2SO-d6) δ1.78 (s, 3, CH3), 2.17 and 2.45 (2 m, 2, 2'CH2), 3.70 (m, 2, 5'CH2), 3.88 (m, 1, 4'H), 4.16 (m, 1, 3'H), 4.8 (br s, 1, 5'OH), 6.05 (dd, 1, 1H), 6.2 (br s, 2 NH2), 7.48 (s, 1, C6H), and 11.24 (br s, 1, NH). Anal. Calcd. for C10H15N3O5 : C, 46.69; H, 5.87; N, 16.33; found: C, 46.55; H, 5.91; N, 16.21.

Provenance & Evidence