반응 #366912

반응 방정식

piperidine

7

3′-Deoxy-5′-O-{6-{{[(9H-fluoren-9-yl)methoxy]carbonyl}amino}hexanyl}-N6,2′-O-bis[2-(4-nitrophenyl)ethoxycarbonyl]adenosine

tetradecanoic acid

TOTU

N-methylmorpholine

NaHCO3

→

3′-Deoxy-5′-O-[6-(tetradecanoylamino)hexanoyl]adenosine

용매

DMF

DMF

CHCl3

반응 조건

후처리

1. 1
   기타(r.t., 2.5 h)
2. 2
   기타Purification by FC (silica gel, 12×3 cm, CHCl3

실험 절차

As described in Preparation 4, with tetradecanoic acid (151 mg, 0.66 mmol), TOTU (67 mg, 0.66 mmol), and N-methylmorpholine (67, 0.66 mmol) in abs. DMF (3 ml; 1 h). Deblocking of 7 (584 mg, 0.6 mmol) with 3% piperidine in abs. DMF (6 ml; 10 min) and addition of above-mentioned soln. (r.t., 2.5 h). Workup with CHCl3 (150 ml) and NaHCO3 soln. (2×70 ml) and reextraction. Purification by FC (silica gel, 12×3 cm, CHCl3, then CHCl3/MeOH 98:2,95:5): 405 mg (70%) of 14. Colorless oil. 1H-NMR (CDCl3): 8.73-8.15 (m, H—C(8), H—C(2), 4 H o to NO2, NH(ade)); 7.47-7.38 (m, 4H m to NO2); 6.12 (d, H—C(1′)); 5.73 (m, H—C(2′)); 5.57 (t, NH(CH2)5CO); 4.68 (m, H—C(4′)); 4.54, 4.43 (2t, 2 OCH2CH2); 4.4-4.2 (m, 2 H—C(5′)); 3.7-3.5 (m, 1 CH2 of NH(CH2)5CO); 3.25-3.1 (m, 2 OCH2CH2, 1 CH2 of NH(CH2)5CO); 2.65, 2.25 (2m, 2 H—C(3′)); 2.27, 2.15 (2t, 2 CH2 of NH(CH2)5CO), 1 CH2 of Me(CH2)12CO); 1.7-1.15 (m, 3 CH2 of NH(CH2)5CO), 11 CH2 of Me(CH2)12CO); 0.87 (t, Me(CH2)12CO).

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