Tetrabutylammonium Fluoride → HCID 86589979, compound

Participants

Reaction Steps

3′-O-[(tertbutyl)dimethylsilyl]-5′-O-[(tertbutyl)diphenylsilyl]-4′-C-(1,1′-diphenylmethylaminomethyl)-2′-deoxyuridine (11) (0.13 g, 0.16 mmol) was treated with tetrabutylammonium fluoride solution (0.45 mL) in tetrahydrofuran (5 mL) according to the procedure used for the preparation of compound (3). The title compound (12) was obtained as a clear glass (0.056 g, 78%). δH(300 MHz, d6-DMSO) 11.25(1H, s, br, N3—H), 7.90(1H, d, H-6), 7.40–7.15(10H, m, Ph2CHNH), 6.19(1H, dd, H-1′), 5.93(1H, d, br, 3′-OH), 5.91(1H, s, br, Ph2CHNH), 5.11(1H, t, br, 5′-OH), 4.78(1H, s, Ph2CHNH), 4.33(1H, dd, H-3′), 3.61(1H, d, H-5′), 2.52–2.49(2H, m, 4′-C—CH2), 2.18(2H, m, H-2′); δC(75.45 MHz, d6-DMSO) 163.13, 150.43, 144.50, 144.25, 140.62, 128.34, 126.97, 126.92, 126.72, 101.60, 88.63, 83.50, 72.0, 66.85, 58.8, 51.15; ES +ve m/z 424(M+H)+.

Provenance & Evidence