Chlorotrimethylsilane → HCID 136132501, compound

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Reaction Steps

2′-O-pentylguanosine (2.3 g) in pyridine (35 ml) was treated with trimethylsilyl chloride (4.15 ml, 5 eq) and isobutyryl chloride (3.4 ml, 5 eq) as per the procedure of Example 4 to yield the product as a foam (2.3 g). An analytical sample was crystallized from EtOAc/Hex. m.p. 178-180° C. 1H NMR (DMSO-d6) δ 0.75 (t, 3, CH3), 1.1 [m, 10, 2×CH2, CH(CH3)2], 1.4 (m, 2, CH2), 2.74 [m, 1, CH(CH3)2], 3.56 (m, 4, OCH2, H-5′), 3.93 (m, 1, H-4′), 4.25 (m, 1), 4.34 (m, 1), 5.05 (t, 1, 5′-OH), 5.17 (d, 1, 3′-OH), 5.88 (d, 1, H-1′), 8.27 (s, 1, H-8), 11.65 (br s, 1, NH) and 12.05 (br s, 1, NH). Anal. Calcd. for C19H29N5O6: C, 53.89; H, 6.90; N, 16.54. Found: 53.75; H, 6.92; N, 16.40

Provenance & Evidence