Tetrahydrofuran → (Tert-butyloxycarbonyl]-6-(amino)-4,5-dihydroxy-7-cyclohexyl-1-heptyne
Reaction equation
[F-].C([N+](C[CH2:16][CH2:17][CH3:18])(CCCC)CCCC)CCC.C(OC([NH:26][C@@H:27]([CH2:45][CH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][CH2:47]1)[C@@H:28]([O:34][Si](C(C)C)(C(C)C)C(C)C)[CH:29]([OH:33])[CH2:30][C:31]#[CH:32])=O)(C)(C)C.CC[O:54][C:55](C)=[O:56].[CH2:58]1COCC1>CCCCCC>[C:17]([O:56][C:55]([C:32]#[C:31][CH2:30][CH:29]([OH:33])[CH:28]([OH:34])[CH:27]([NH2:26])[CH2:45][CH:46]1[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51]1)=[O:54])([CH3:16])([CH3:18])[CH3:58]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
A 1.0M tetra n-butylammonium fluoride solution (21.5 mmol) in THF (21.5 mL) was added dropwise to the title alkyne of Step 5 (5.41 mmol) at room temperature. Thin-layer chromatography (TLC) (20% EtOAc in hexane) showed the reaction was completed in 1 h. The solution was concentrated and EtOAc (160 mL) was added. The solution was washed with H2O (3×60 mL), brine (100 mL), and then dried over MgSO4. After evaporation, the residue (a clear, yellow liquid) was purified by column chromatography and the diastereomers were separated. The major isomer (Rf 0.16, 1.76 g, 53% yield) was consistent with the proposed structure from 1H, 13C and APT NMR spectral data.
Workup
- concentrationThe solution was concentrated
- additionEtOAc (160 mL) was added
- washThe solution was washed with H2O (3×60 mL), brine (100 mL)
- dry with materialdried over MgSO4
- customAfter evaporation
- customthe residue (a clear, yellow liquid) was purified by column chromatography
- customthe diastereomers were separated
Sources & evidence
- ORD record
- ord-d997dbd0bebc4f64b747e772afe6e6d8
- Source dataset
- uspto-grants-1994_07
- Patent number
- US05330996
Reaction notes
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