Toluene → HCID 86761231, 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:52]3[N:51]=[C:45]([NH:46][C:47](=[S:50])[NH:48][CH3:49])[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:37]1([N:30]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[C:29]([O:28][C:27]2[C:26]3[N:25]=[CH:24][N:23]([C:52]=3[N:51]=[C:45]([NH:46][C:47](=[S:50])[NH:48][CH3:49])[N:44]=2)[C@@H:11]2[O:12][C@H:13]([CH2:14][OH:15])[C@@H:9]([OH:8])[CH2:10]2)=[O:43])[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
The above-obtained 3′,5′-bis-O-(tert-butyldimethylsilyl)-6-O-diphenylcarbamoyl-2-N-methylthiocarbamoyldeoxyguanosine (900 mg, 1.17 mmol) was azeotroped with anhydrous tetrahydrofuran three times and dissolved in anhydrous tetrahydrofuran (6.0 mL), and triethylamine 3 hydrogen fluoride (574 μL, 3.51 mmol) was added thereto. The mixture was stirred at room temperature overnight, and then toluene (5 mL) was added thereto. The solvent was evaporated under reduced pressure. To the residue, methanol (5 mL) and hexane (25 mL) were added for precipitation. The resulting precipitate was purified by filtration to give 6-O-diphenylcarbamoyl-2-N-methylthiocarbamoyldeoxyguanosine (504 mg, 80%).
Workup
- customThe solvent was evaporated under reduced pressure
- additionTo the residue, methanol (5 mL) and hexane (25 mL) were added for precipitation
- filtrationThe resulting precipitate was purified by filtration
Sources & evidence
- ORD record
- ord-8c7eacf5367f4e24b5a7151454483938
- Source dataset
- uspto-grants-2010_12
- Patent number
- US07851157B1
Reaction notes
Loading…