Ethyl Acetate → 3'-Deoxy-5'-O-(4-methoxytrityl)-3'-(iodomethyl)-2'-O-(2-methoxyethyl)-5-methyluridine
Reaction equation
[I:1][CH2:2][C@@H:3]1[C@@H:7]([CH2:8][OH:9])[O:6][C@@H:5]([N:10]2[CH:17]=[C:16]([CH3:18])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[C@@H:4]1[O:19][CH2:20][CH2:21][O:22][CH3:23].C(N([CH:30]([CH3:32])[CH3:31])CC)(C)C.[CH2:33]([C:42](Cl)([C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:34]1C=CC(OC)=C[CH:35]=1.[C:56](OCC)(=[O:58])C>C1COCC1>[CH3:56][O:58][C:31]1[CH:30]=[CH:32][C:33]([C:42]([O:9][CH2:8][C@H:7]2[O:6][C@@H:5]([N:10]3[CH:17]=[C:16]([CH3:18])[C:14](=[O:15])[NH:13][C:11]3=[O:12])[C@H:4]([O:19][CH2:20][CH2:21][O:22][CH3:23])[C@@H:3]2[CH2:2][I:1])([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:49]2[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=2)=[CH:34][CH:35]=1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A mixture of 3′-deoxy-3′-(iodomethyl)-2′-O-(2-methoxyethyl)-5-methyluridine (472 mg, 1.1 mmol), diisopropylethylamine (0.79 mL, 0.586 g, 4.5 mmol), and p-anisyl chlorodiphenyl methane (4′-methoxytrityl chloride, MMT-Cl) (1.32 g, 4.27 mmol) in 6 mL of ethyl acetate and 4 mL of THF was stirred at rt for 48 h. The reaction mixture was diluted with ethyl acetate and washed with water, followed by brine. The organic phase was dried (Na2SO4) and concentrated. The crude product was purified by flash chromatography on a silica gel column. Gradient elution with 3:1, 2:1, 1:1, and then 1:3 hexanes-EtOAc provided 690 mg of the title compound as a white foam.
Workup
- washwashed with water
- dry with materialThe organic phase was dried (Na2SO4)
- concentrationconcentrated
- customThe crude product was purified by flash chromatography on a silica gel column
- washGradient elution with 3:1, 2:1, 1:1
Sources & evidence
- ORD record
- ord-8bd3de0b5dab4c6484611c8595013f12
- Source dataset
- uspto-grants-2006_09
- Patent number
- US07105499B2
Reaction notes
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