Tetrabutylammonium Fluoride → HCID 86589979, compound
Reaction equation
C([Si](C)(C)[O:6][C@@H:7]1[C@@:11]([CH:31]([NH:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[NH:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([CH2:12][O:13][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[O:10][C@@H:9]([N:48]2[CH:55]=[CH:54][C:52](=[O:53])[NH:51][C:49]2=[O:50])[CH2:8]1)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(CNC([C@]2(CO)O[C@@H](N3C=C(C)C(=O)NC3=O)C[C@@H]2O)NCC2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[C:34]1([CH2:33][NH:32][CH:31]([C@:11]2([CH2:12][OH:13])[O:10][C@@H:9]([N:48]3[CH:55]=[CH:54][C:52](=[O:53])[NH:51][C:49]3=[O:50])[CH2:8][C@@H:7]2[OH:6])[NH:40][CH2:41][C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3′-O-[(tertbutyl)dimethylsilyl]-5′-O-[(tertbutyl)diphenylsilyl]-4′-C-(1,1′-diphenylmethylaminomethyl)-2′-deoxyuridine (11) (0.13 g, 0.16 mmol) was treated with tetrabutylammonium fluoride solution (0.45 mL) in tetrahydrofuran (5 mL) according to the procedure used for the preparation of compound (3). The title compound (12) was obtained as a clear glass (0.056 g, 78%). δH(300 MHz, d6-DMSO) 11.25(1H, s, br, N3—H), 7.90(1H, d, H-6), 7.40–7.15(10H, m, Ph2CHNH), 6.19(1H, dd, H-1′), 5.93(1H, d, br, 3′-OH), 5.91(1H, s, br, Ph2CHNH), 5.11(1H, t, br, 5′-OH), 4.78(1H, s, Ph2CHNH), 4.33(1H, dd, H-3′), 3.61(1H, d, H-5′), 2.52–2.49(2H, m, 4′-C—CH2), 2.18(2H, m, H-2′); δC(75.45 MHz, d6-DMSO) 163.13, 150.43, 144.50, 144.25, 140.62, 128.34, 126.97, 126.92, 126.72, 101.60, 88.63, 83.50, 72.0, 66.85, 58.8, 51.15; ES +ve m/z 424(M+H)+.
Sources & evidence
- ORD record
- ord-8c5835ed9058457aa9bbc2561f7d57c9
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07078499B2
Reaction notes
Loading…