Acetic Acid → HCID 22866807, compound

HRID 1899796Notes

Reaction equation

[Si:1]([O:8][C:9]([C:11]([F:35])([F:34])[C@@:12](C(=O)C1C=CC=CC=1)([C@@H:14]([CH:16]([C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:17])[OH:15])[OH:13])=[O:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].CC(C)([O-])C.[K+].C(O)(=O)C>O1CCCC1.C(OCC)(=O)C>[Si:1]([O:8][C:9]([C:11]([F:34])([F:35])[C@@H:12]([C@@H:14]([CH:16]([C:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:17])[OH:15])[OH:13])=[O:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 0.97 g (2.0 mmol) of 1-(t-butyldimethylsilyloxy)-3,5-bis(benzoyl)-2-deoxy-2,2-difluororibose in tetrahydrofuran (40 ml) cooled to -78° C. were added 4.0 ml of a 1M solution of potassium t-butoxide in tetrahydrofuran (4.0 mmol) dropwise. The reaction mixture was stirred 15 minutes at -78° C. and was then quenched with 0.45 ml glacial acetic acid (8.0 mmol). The reaction mixture was diluted with ethyl acetate (100 ml) and washed with brine (50 ml). The separated organic layer was dried with sodium sulfate and evaporated under reduced pressure. The resulting residue was chromatographed on silica gel and eluted with hexane containing 10-15% ethyl acetate. The product fractions were combined and concentrated under reduced pressure to yield 0.724 g (93%) of 1-(t-butyldimethylsilyloxy)-5-benzoyl-2-deoxy-2,2-difluororibose. Mass spec.: m/e=389=P+1, m/e=331=P-t-butyl.

Workup

washwashed with brine (50 ml)
dry with materialThe separated organic layer was dried with sodium sulfate
customevaporated under reduced pressure
customThe resulting residue was chromatographed on silica gel
washeluted with hexane containing 10-15% ethyl acetate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-e5f7b347b224495aa2c37d69dbe62ed6
Source dataset: uspto-grants-1996_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05574021

Reaction notes

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