Chlorotrimethylsilane → N2-Isobutyryl-2'-O-nonylguanosine

Participants

Reaction Steps

2′-O-nonylguanosine (14.7 g) in pyridine (360 ml) was treated with trimethylsilyl chloride (23.4 ml) and isobutyryl chloride (30.6 ml) as per the procedure of Example 4 to yield crude product (37 g). The crude material was purified by silica gel chromatography (eluted with 90/10 CHCl3/MeOH) to yield 14.6 g of product re-crystallized from EtOAc. m.p. 168-169° C. 1H NMR (DMSO-d6) δ 0.85 [t, 3, CH3(nonyl)], 1.14 [m, 18, O—CH2CH2(CH2)6, CH(CH3)2], 1.40 [m, 2, O—CH2CH2(CH2)6], 2.79 [m, 1, CH(CH3)2], 3.31-3.63 (m, 4, H-5′, O—CH2(CH2)7]; 3.96 (m, 1, H-4′), 4.27-4.37 (m, 2, H-2′, H-3′); 5.10 (t, 1, 5′-OH, J=5 Hz), 5.18 (d, 1, 3′-OH, J=4 Hz), 5.91 (d, 1, H-1′, J=6.6 Hz), 8.31 (s, 1, 8-H), 11.73 (s, 1, C2 amide) and 12.11 (s, 1, N1 amide). Anal. Calcd. for C23H37N5O6: C, 57.60; H, 7.78; N, 14.60. Found: C, 57.63; H, 7.92; N, 14.62.

Provenance & Evidence