Tetrabutylammonium Fluoride → 8-(3-Pyridinyl)adenosine
Reaction equation
[Si]([O:8][C@@H:9]1[C@H:13]([O:14][Si](C(C)(C)C)(C)C)[C@@H:12]([CH2:22][O:23][Si](C(C)(C)C)(C)C)[O:11][C@H:10]1[N:31]1[C:40]2[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=2[N:33]=[C:32]1[C:41]1[CH:42]=[N:43][CH:44]=[CH:45][CH:46]=1)(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[N:43]1[CH:44]=[CH:45][CH:46]=[C:41]([C:32]2[N:31]([C:40]3[N:39]=[CH:38][N:37]=[C:35]([NH2:36])[C:34]=3[N:33]=2)[C@@H:10]2[O:11][C@H:12]([CH2:22][OH:23])[C@@H:13]([OH:14])[C@H:9]2[OH:8])[CH:42]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 2′,3′,5′-tris-O-(tert-butyldimethylsilyl)-8-(3-pyridinyl)adenosine (16c) (0.56 g, 0.82 mmol) and TBAF (0.85 g, 3.26 mmol) in THF (31 ml) under argon was stirred at room temperature overnight. The solvent was distilled off and the residual material dissolved in MeOH (10 ml). The solution was left at 0° C. overnight and the title compound isolated by filtration. 13C NMR: (75 MHz, DMSO); δ 62.27 (C-5′), 71.13/71.62 (C-2′, C-3′), 86.95/89.27 (C-4, C-1), 119.33/123.69/125.71/137.20/148.20/149.80/149.85/150.88/152.33/156.34 (C-5, C-5″, C-3″, C-4″, C-6, C-8, C-6″, C-2″, C-2, C-4). MS (EI): 344 (M, 2%), 255 (5), 241 (5), 213 (22), 212 (100), 211 (5) 185 (12), 104 (12).