Methanol → 5'-O-tert-butyldiphenylsilyl-N6-benzoyl-2'-O-(2,3-dihydroxypropyl)-adenosine
Reaction equation
C([O:4][C@@H:5]1[C@@H:9]([CH2:10][O:11][Si:12]([C:25]([CH3:28])([CH3:27])[CH3:26])([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:8][C@@H:7]([N:29]2[C:46]3[N:45]=[CH:44][N:43]=[C:33]([NH:34][C:35](=[O:42])[C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:32]=3[N:31]=[CH:30]2)[C@@H:6]1[OH:47])C=C.[CH3:48][N+]1([O-])CCOCC1.CO.C(OCC)(=O)C.[O:64]1CC[O:67][CH2:66][CH2:65]1>C(Cl)Cl>[Si:12]([O:11][CH2:10][C@H:9]1[O:8][C@@H:7]([N:29]2[C:46]3[N:45]=[CH:44][N:43]=[C:33]([NH:34][C:35](=[O:42])[C:36]4[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=4)[C:32]=3[N:31]=[CH:30]2)[C@H:6]([O:47][CH2:48][CH:66]([OH:67])[CH2:65][OH:64])[C@@H:5]1[OH:4])([C:25]([CH3:28])([CH3:27])[CH3:26])([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
3′-O-allyl-5′-O-tert-butyldiphenylsilyl-N6-benzoyl-adenosine (5.5 g, 8.46 mmol), 4-methylmorpholine N-oxide (1.43 g, 12.18 mmol) were dissolved in dioxane (45.42 mL). 4% aqueous solution of OSO4 (1.99 mL, 0.31 mmol) was added. The reaction mixture was protected from light and stirred for 3 hrs. Reaction was monitored by TLC (5% MeOH in CH2Cl2). Ethyl acetate (100 mL) was added and the resulting reaction mixture was washed with water (1×50 mL). Ethyl acetate layer was dried over anhydrous Na2SO4 and evaporated to get the title compound (5.9 g) and used for next step without purification. Rf 0.17 (5% MeOH in CH2Cl2)
Workup
- customReaction
- customthe resulting reaction mixture
- washwas washed with water (1×50 mL)
- dry with materialEthyl acetate layer was dried over anhydrous Na2SO4
- customevaporated
Sources & evidence
- ORD record
- ord-543f1077ea234f10bdfaa2097025d5be
- Source dataset
- uspto-grants-2005_02
- Patent number
- US06849723B2
Reaction notes
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