(1R,3R,4R,7R)-7-Benzyloxy-1-(4,4'-dimethoxytrityloxymethyl)-3-(Thymin-1-yl)-2,5-Dioxabicyclo[2.2.1]Heptane → (1S,3R,4R,7R)-7-hydroxy-1-hydroxymethyl-3-(thymin-1-yl)-2,5-dioxabicyclo [2.2.1]heptane
Reaction equation
C([O:8][C@@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:25][O:26]C(C1C=CC=CC=1)(C1C=CC(OC)=CC=1)C1C=CC(OC)=CC=1)[O:11][C@H:12]2[N:16]1[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]1=[O:18])C1C=CC=CC=1>CO.[Pd]>[OH:8][C@@H:9]1[C@H:13]2[O:14][CH2:15][C@:10]1([CH2:25][OH:26])[O:11][C@H:12]2[N:16]1[CH:24]=[C:22]([CH3:23])[C:20](=[O:21])[NH:19][C:17]1=[O:18]Participants
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
Nucleoside 8 (3.09 g, 4.66 mmol) was dissolved in methanol (40 cm3) and 10% palladium on carbon (3 g, suspended in methanol (20 cm3)) was added. The mixture was degassed and stirred under an atmosphere of hydrogen. After 26 h, the mixture was filtered (silica gel, washed with dichloromethane/methanol (700 cm3; 1:3, v/v)) and the volume of the filtrate was concentrated to 25% of its initial volume. After repeated filtration, the filtrate was evaporated to dryness under reduced pressure and the residue was subjected to column chromatography on silica gel using dichloromethane/methanol (5–12% methanol, v/v) as eluent furnishing nucleoside 9 (1.03 g, 82%) as a white solid material after evaporation of the solvents under reduced pressure.
Workup
- customThe mixture was degassed
- filtrationthe mixture was filtered (silica gel
- washwashed with dichloromethane/methanol (700 cm3
- concentration1:3, v/v)) and the volume of the filtrate was concentrated to 25% of its initial volume
- filtrationfiltration
- customthe filtrate was evaporated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-d941bde6761f4c328e8182f61055248b
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07084125B2
Reaction notes
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