Acetic Acid → HCID 86749969, compound
Reaction equation
[C:1]([C:5]([O:7][C:8]([C:10]([F:24])([F:23])[C@@:11](C(=O)C)([C@@H:13]([CH:15]([C:17](=[O:19])[CH3:18])[OH:16])[OH:14])[OH:12])=[O:9])=[O:6])([CH3:4])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].C(O)(=O)C>O1CCCC1>[C:1]([C:5]([O:7][C:8]([C:10]([F:23])([F:24])[C@@H:11]([C@@H:13]([CH:15]([C:17](=[O:19])[CH3:18])[OH:16])[OH:14])[OH:12])=[O:9])=[O:6])([CH3:4])([CH3:2])[CH3:3]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -65 °C
Procedure
To a solution of 0.5 g (approximately 1 mmol) crude 1-(t-butylcarbonyloxy)-3,5-bis(acetyl)-2-deoxy-2,2-difluororibose in tetrahydrofuran (5 ml) cooled to -65° C. were added 2.0 ml of a 1M solution of potassium t-butoxide in tetrahydrofuran (2 mmol) dropwise and the reaction mixture stirred 1 hour at -65° C. The reaction was then quenched with 0.23 ml of glacial acetic acid (4 mmol) and allowed to warm to room temperature. The reaction mixture was concentrated under reduced pressure to give 0.43 gm 1-(t-butylcarbonyloxy)-5-acetyl-2-deoxy-2,2-difluororibose. Mass spec. m/e=390=P+1.
Workup
- temperatureto warm to room temperature
- concentrationThe reaction mixture was concentrated under reduced pressure
Sources & evidence
- ORD record
- ord-2452ee2128cb4d91a57bf8c996e17171
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05574021
Reaction notes
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