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) δ0.85 [t, 3, CH3 (nonyl)], 1.14 [m, 18, O--CH2CH2 (CH2)6, CH(CH3)2 ], 1.40 [m, 2, O--CH2CH-2 (CH2)6 ], 2.79 [m, 1, CH(CH3)2 ], 3.31-3.63 (m, 4, H5', 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