Réaction #302905

Équation de réaction

MeOH

10b

1-[2-Deoxy-3-O-(t-butyldimethyl-silyl)-4-ethynyl-α-L-erythro-pentofuranosyl]thymine

→

4′-allylthymidine

Conditions de réaction

Mode opératoire

Physical data for 10b: mp 96-98° C.; UV (MeOH): λmax 267 nm (ε9300), λmin 235 nm (ε1700). 1H NMR (CDCl3) δ0.08 and 0.13 (6H, each as s, SiMe), 0.89 (9H, s, SiBu-t), 1.93 (3H, d, J6,CH3=0.9 Hz, Me), 2.12-2.17 (1H, m, H-2′a), 2.63 (1H, br, OH), 2.71-2.77 (1H, m, H-2′b), 2.75 (1H, s, ethynyl), 3.67 (1H, d, Jgem=11.5 Hz, H-5′a), 3.74 (1H, d, Jgem=11.5 Hz, H-5′b), 4.47 (1H, t, J2′a,3′=J2′b,3′=5.3 Hz, H-3′), 6.30 (1H, dd, J1′,2′a=4.8 Hz and J1′,2′b=6.9 Hz, H-1′), 7.80 (1H, d, J6,CH3=0.9 Hz, H-6), 9.00 (1H, brs, NH); FAB-MS m/z 381 (M++H). Anal. Calcd for C18H28N2O5Si: C, 56.82; H, 7.42; N, 7.36. Found: C, 56.57; H, 7.58; N, 7.19.

Source