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

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Reaction Steps

2′-O-Octadecylguanosine (1.9 g) in pyridine (150 ml) was treated with trimethylsilyl chloride (2 g, 5 eq) and isobutyryl chloride (2 g, 5 eq) as per the procedure of Example 4. The product was purified by silica gel chromatography (eluted with 3% MeOH/EtOAc) to yield 1.2 g of product. 1H NMR (DMSO-d6) δ 0.85 [t, 3, CH3], 1.15 [m, 38, O—CH2CH2(CH2)16, CH(CH3)2], 2.77 [m, 1, CH(CH3)2], 4.25 (m, 2, 2′H, 3′H); 5.08 (t, 1, 5′-OH), 5.12 (d, 1, 3′-OH), 5.87 (d, 1, 1′-H), 8.27 (s, 1, 8-H), 11.68 (s, 1, NH2) and 12.08 (s, 1, NH2). Anal. Calcd. for C32H55N5O6: C, 63.47; H, 9.09; N, 11.57. Found: C, 63.53; H, 9.20; N, 11.52.

Provenance & Evidence