Tetrabutylammonium Fluoride → HCID 86684715, compound
Reaction equation
[Si]([C@@:8]1([OH:48])[C@@H:12]([CH2:13][O:14][Si](C(C)(C)C)(C)C)[O:11][C@@H:10]([N:22]2[CH:29]=[C:28]([CH2:30][O:31][C@H:32]([C:37]3[CH:42]=[C:41]([O:43][CH3:44])[CH:40]=[CH:39][C:38]=3[N+:45]([O-:47])=[O:46])[C:33]([CH3:36])([CH3:35])[CH3:34])[C:26]([NH2:27])=[N:25][C:23]2=[O:24])[CH2:9]1)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH3:44][O:43][C:41]1[CH:40]=[CH:39][C:38]([N+:45]([O-:47])=[O:46])=[C:37]([C@@H:32]([O:31][CH2:30][C:28]2[C:26]([NH2:27])=[N:25][C:23](=[O:24])[N:22]([CH:29]=2)[C@@H:10]2[O:11][C@H:12]([CH2:13][OH:14])[C@@H:8]([OH:48])[CH2:9]2)[C:33]([CH3:36])([CH3:35])[CH3:34])[CH:42]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of compound 49 (130 mg, 0.18 mmol) in THF (10 mL), n-Bu4NF (141 mg, 0.44 mmol) was added. The mixture was stirred at room temperature for four hours, concentrated in vacuo, and the residue was purified by silica gel column chromatography to yield 5-[(S)-1-(5-methoxy-2-nitrophenyl)-2,2-dimethyl-propyloxy]methyl-2′-deoxycytidine 50 (72 mg, 82%). 1H NMR (400 MHz, DMSO-d6): δ 7.99 (d, J=8.0 Hz, 1H, Ph-H), 7.65 (s, 1H, H-6), 7.42 (br s, 1H, D2O exchangeable, NH2a), 7.06 (m, 2H, Ph-H), 6.72 (br s, 1H, D2O exchangeable, NH2b), 6.11 (t, 1H, J=6.4 Hz, H-1′), 5.17 (d, 1H, D2O exchangeable, 3′-OH), 5.12 (s, 1H, Ph-CH), 4.78 (t, 1H, D2O exchangeable, 5′-OH), 4.25 (d, 1H, J=12.4 Hz, 5-CH2a), 4.15 (m, 1H, H-3′), 4.05 (d, 1H, J=12.4 Hz, 5-CH2b), 3.87 (s, 3H, OCH3), 3.72 (m, 1H, H-4′), 3.44 (m, 2H, H-5′), 3.76 (dd, 1H, J=2.8 Hz, H-5′b), 2.08 (m, 1H, H-2′a), 1.95 (m, 1H, H-2′b), 0.77 (s, 9H, C(CH3)3).
Workup
- concentrationconcentrated in vacuo
- customthe residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-490f32ed99d24a24a9294c57798d25ca
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09399798B2
Reaction notes
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