Technology Process of (3aR,4R,5R,6aS)-hexahydro-5-tert-butyldimethylsilyloxy-4-[(1E,3S)-3-tert-butyldimethylsilyloxy-(1E)-octenyl]-2H-cyclopenta[β]furan-2-one
There total 1 articles about (3aR,4R,5R,6aS)-hexahydro-5-tert-butyldimethylsilyloxy-4-[(1E,3S)-3-tert-butyldimethylsilyloxy-(1E)-octenyl]-2H-cyclopenta[β]furan-2-one which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
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Multi-step reaction with 5 steps
1.1: formic acid; sulfuric acid / 24 h / 80 °C
1.2: 2 h / 0 - 20 °C
2.1: [bis(acetoxy)iodo]benzene; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; N,N-dimethyl acetamide / 6 h / 20 °C
3.1: sodium hydride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
3.2: 6 h / 0 - 20 °C / Inert atmosphere
4.1: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethylsulfide borane complex / tetrahydrofuran; toluene / 1 h / -30 °C
5.1: 1H-imidazole / dichloromethane / 18 h / 20 °C
With
1H-imidazole; formic acid; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; dimethylsulfide borane complex; sulfuric acid; sodium hydride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; dichloromethane; N,N-dimethyl acetamide; toluene;
3.1: |Horner-Wadsworth-Emmons Olefination / 3.2: |Horner-Wadsworth-Emmons Olefination / 4.1: |Corey-Bakshi-Shibata Reduction;
DOI:10.1002/anie.201902371
- Guidance literature:
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Multi-step reaction with 4 steps
1.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C
2.1: potassium hexamethylsilazane / tetrahydrofuran / 0.67 h / 0 °C / Inert atmosphere
2.2: 4 h / -20 - -10 °C / Inert atmosphere
3.1: Dess-Martin periodane / dichloromethane / 20 °C
4.1: pyridine hydrogenfluoride / acetonitrile; water / 4 h / 0 - 20 °C
With
potassium hexamethylsilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride;
In
tetrahydrofuran; dichloromethane; water; acetonitrile;
DOI:10.1002/anie.201902371
- Guidance literature:
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Multi-step reaction with 3 steps
1: 1.) potassium hydroxide; 2.) iodomethane, imidazole / 1.) alcohol; 2.) dimethylformamide, r.t., 11 h
2: 1.) LDA / 1.) THF, 0 deg C, 1.0 h; 2.) THF, 0 deg C - r.t., 2.5 h
3: 66 percent / NaH / dimethylsulfoxide; 1,2-dimethoxy-ethane / 1 h / 0 °C
With
1H-imidazole; potassium hydroxide; sodium hydride; lithium diisopropyl amide; methyl iodide;
In
1,2-dimethoxyethane; dimethyl sulfoxide;
DOI:10.1246/cl.1985.557
