Benzyl Alcohol → HCID 11187700, compound
Reaction equation
[CH2:1]([OH:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[C@@H:13]1[O:25][C@H:24]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[C@@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@H:14]1[O:15][C:16](=[O:18])[CH3:17])(=O)C.O>C(OCC)(=O)C.[Cl-].[Zn+2].[Cl-]>[C:16]([O:15][C@@H:14]1[C@H:19]([O:20][C:21](=[O:23])[CH3:22])[C@@H:24]([CH2:26][O:27][C:28](=[O:30])[CH3:29])[O:25][C@H:13]1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)(=[O:18])[CH3:17]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 60 °C
Procedure
Benzyl alcohol (0.57 mL, 5.5 mmol) was added to a solution of β-D-ribofuranose-1,2,3,5-tetraacetate (1.59 g, 5 mmol) and zinc chloride (681.4 mg, 5 mmol) in ethyl acetate (8 mL), and the mixture was stirred with heating to 60° C. for 2 hours. After cooling the mixture to ambient temperature, water (2 mL) was added to the resulting solution, for layer separation. The resulting organic layer was washed twice with aqueous 7% sodium hydrogen carbonate solution (2 mL) and subsequently concentrated under reduced pressure. The resulting oil was purified by silica gel column chromatography, to recover the desired 1-O-benzyl-β-D-ribofuranose-2,3,5-triacetate (1.56 g; yield of 85.1%) as a colorless solid. Melting point: 65° C.
Workup
- temperatureAfter cooling the mixture to ambient temperature
- washThe resulting organic layer was washed twice with aqueous 7% sodium hydrogen carbonate solution (2 mL)
- concentrationsubsequently concentrated under reduced pressure
- customThe resulting oil was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-71b74314d0c341a98b698d8cd648eb2d
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06800742B2
Reaction notes
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