Technology Process of (2S,3R,4S,5R,6R)-2-((E)-(S)-5-Benzyloxy-4-methoxy-pent-1-enyl)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-4-ol
There total 11 articles about (2S,3R,4S,5R,6R)-2-((E)-(S)-5-Benzyloxy-4-methoxy-pent-1-enyl)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-3-methoxy-propyl]-2-methoxy-3,5-dimethyl-tetrahydro-pyran-4-ol which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
Multi-step reaction with 6 steps
1.1: nBuLi / hexane; tetrahydrofuran / 0.17 h
1.2: BF3*OEt2 / tetrahydrofuran; hexane / 2 h / -78 °C
2.1: lithium hexamethyldisilazide / tetrahydrofuran / 16 h / 40 °C
3.1: 8.8 g / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h
4.1: LiEt3BH; Cp2ZrCl2 / tetrahydrofuran / 0.25 h
4.2: 88 percent / N-iodosuccinimide / tetrahydrofuran / 0.17 h
5.1: tBuLi / pentane; diethyl ether / 1.5 h / -78 °C
5.2: diethyl ether; pentane; toluene / 3.5 h
6.1: 1.58 g / pyridinium p-toluene sulfonate / CH2Cl2 / 0.5 h / 0 °C
With
n-butyllithium; zirconocene dichloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; lithium triethylborohydride; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; pentane;
DOI:10.1002/chem.200600461
- Guidance literature:
-
Multi-step reaction with 3 steps
1.1: LiEt3BH; Cp2ZrCl2 / tetrahydrofuran / 0.25 h
1.2: 88 percent / N-iodosuccinimide / tetrahydrofuran / 0.17 h
2.1: tBuLi / pentane; diethyl ether / 1.5 h / -78 °C
2.2: diethyl ether; pentane; toluene / 3.5 h
3.1: 1.58 g / pyridinium p-toluene sulfonate / CH2Cl2 / 0.5 h / 0 °C
With
zirconocene dichloride; tert.-butyl lithium; pyridinium p-toluenesulfonate; lithium triethylborohydride;
In
tetrahydrofuran; diethyl ether; dichloromethane; pentane;
DOI:10.1002/chem.200600461
- Guidance literature:
-
Multi-step reaction with 4 steps
1.1: 8.8 g / tetrabutylammonium fluoride / tetrahydrofuran / 1.5 h
2.1: LiEt3BH; Cp2ZrCl2 / tetrahydrofuran / 0.25 h
2.2: 88 percent / N-iodosuccinimide / tetrahydrofuran / 0.17 h
3.1: tBuLi / pentane; diethyl ether / 1.5 h / -78 °C
3.2: diethyl ether; pentane; toluene / 3.5 h
4.1: 1.58 g / pyridinium p-toluene sulfonate / CH2Cl2 / 0.5 h / 0 °C
With
zirconocene dichloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; lithium triethylborohydride;
In
tetrahydrofuran; diethyl ether; dichloromethane; pentane;
DOI:10.1002/chem.200600461
