Toluene → HCID 86761229, compound
Reaction equation
[Si]([O:8][C@@H:9]1[C@@H:13]([CH2:14][O:15][Si](C(C)(C)C)(C)C)[O:12][C@@H:11]([N:23]2[C:51]3[N:50]=[C:45]([NH:46][C:47](=[O:49])[NH2:48])[N:44]=[C:27]([O:28][C:29](=[O:43])[N:30]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=4)[C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[C:26]=3[N:25]=[CH:24]2)[CH2:10]1)(C(C)(C)C)(C)C.COC1C=CC(C(OC[C@H]2O[C@@H](N3C4N=C(NC(=O)NC)N=C(OC(=O)N(C5C=CC=CC=5)C5C=CC=CC=5)C=4N=C3)C[C@@H]2O)(C2C=CC=CC=2)C2C=CC(OC)=CC=2)=CC=1.C1(C)C=CC=CC=1>O1CCCC1>[C:47]([NH:46][C:45]1[N:44]=[C:27]([O:28][C:29](=[O:43])[N:30]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:26]2[N:25]=[CH:24][N:23]([C:51]=2[N:50]=1)[C@@H:11]1[O:12][C@H:13]([CH2:14][OH:15])[C@@H:9]([OH:8])[CH2:10]1)(=[O:49])[NH2:48]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The above-obtained 3′,5′-bis-O-(tert-butyldimethylsilyl)-2-N-carbamoyl-6-O-diphenylcarbamoyldeoxyguanosine (1.53 g, 2.09 mmol) was azeotroped with anhydrous tetrahydrofuran three times and dissolved in anhydrous tetrahydrofuran (10 mL), and triethylamine 3 hydrogen fluoride (1.02 mL, 6.27 mmol) was added thereto. The mixture was stirred at room temperature overnight, and then toluene (10 mL) was added thereto. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (N60: spherical neutral silica gel) with methanol/4% to 10% chloroform to give 2-N-carbamoyl-6-O-diphenylcarbamoyldeoxyguanosine (1.21 g, quant).
Workup
- customThe solvent was evaporated under reduced pressure
- customthe residue was purified by silica gel column chromatography (N60: spherical neutral silica gel) with methanol/4% to 10% chloroform
Sources & evidence
- ORD record
- ord-61db205626c84350b4faf6bd4f6e088e
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851157B1
Reaction notes
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