Technology Process of (4'R,5'R,7'E)-2-[4'-(tert-butyldiphenylsilyloxy)-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-1,3-dithiane
There total 13 articles about (4'R,5'R,7'E)-2-[4'-(tert-butyldiphenylsilyloxy)-5'-methyl-8'-phenyl-oct-7'-en-1'-yl]-1,3-dithiane which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: Bu2BOTf; Et3N / CH2Cl2 / -78 - 0 °C
1.2: CH2Cl2 / -78 - 20 °C
1.3: 88 percent / aq. H2O2 / methanol; CH2Cl2; aq. phosphate buffer / 0 - 20 °C
2.1: 81 percent / imidazole / dimethylformamide / 23 h
3.1: 62 percent / LiBH4 / tetrahydrofuran; methanol / 0 - 20 °C
4.1: 89 percent / pyridine / CH2Cl2 / 24 h
5.1: 98 percent / dimethylsulfoxide / 20 h / 60 °C
6.1: DIBAL-H / CH2Cl2 / 1.58 h / -78 °C
7.1: 14.5 g / aq. H2SO4; aq. NH4Cl / 0.33 h / 20 °C
8.1: 95 percent / BCl3*SMe2 / CH2Cl2 / 1.5 h
9.1: 94 percent / Dess-Martin periodinane / CH2Cl2 / 0.08 h
10.1: 100 percent / BF3*OEt2 / CH2Cl2 / 12 h
With
pyridine; 1H-imidazole; lithium borohydride; boron trichloride - methyl sulfide complex; di-n-butylboryl trifluoromethanesulfonate; sulfuric acid; boron trifluoride diethyl etherate; diisobutylaluminium hydride; ammonium chloride; Dess-Martin periodane; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
8.1: Julia olefination;
DOI:10.1016/S0040-4020(02)01514-4
- Guidance literature:
-
Multi-step reaction with 10 steps
1: 81 percent / imidazole / dimethylformamide / 23 h
2: 62 percent / LiBH4 / tetrahydrofuran; methanol / 0 - 20 °C
3: 89 percent / pyridine / CH2Cl2 / 24 h
4: 98 percent / dimethylsulfoxide / 20 h / 60 °C
5: DIBAL-H / CH2Cl2 / 1.58 h / -78 °C
6: 14.5 g / aq. H2SO4; aq. NH4Cl / 0.33 h / 20 °C
7: 95 percent / BCl3*SMe2 / CH2Cl2 / 1.5 h
8: 94 percent / Dess-Martin periodinane / CH2Cl2 / 0.08 h
9: 100 percent / BF3*OEt2 / CH2Cl2 / 12 h
With
pyridine; 1H-imidazole; lithium borohydride; boron trichloride - methyl sulfide complex; sulfuric acid; boron trifluoride diethyl etherate; diisobutylaluminium hydride; ammonium chloride; Dess-Martin periodane;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
7: Julia olefination;
DOI:10.1016/S0040-4020(02)01514-4
