Technology Process of 4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-6,11-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-yn-1-ol
There total 36 articles about 4-{(2R,6R)-6-[(7E,12E)-(2S,6S,10S,11S)-6,11-Bis-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-2-methyl-13-((S)-4-methyl-3,6-dihydro-2H-pyran-2-yl)-4-methylene-trideca-7,12-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-yn-1-ol which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
With
potassium carbonate;
In
tetrahydrofuran; methanol;
at 20 ℃;
DOI:10.1002/anie.200500029
- Guidance literature:
-
Multi-step reaction with 8 steps
1: PPh3 / CH2Cl2 / 0 °C
2: 86 percent / PPh3 / Pd(OAc)2 / tetrahydrofuran / 50 °C
3: 99 percent / PPTS / tetrahydrofuran; acetonitrile / 20 °C
4: 86 percent / SnCl4 / CH2Cl2 / -78 °C
5: 86 percent / Dess-Martin periodinane
6: 92 percent / BH3*THF; (R)-Corey-Bakshi-Shibata oxazaborolidine reagent / tetrahydrofuran / -40 °C
7: 95 percent / imidazole / dimethylformamide / 20 °C
8: 93 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C
With
1H-imidazole; borane-THF; (R)-Corey-Bakshi-Shibata oxazaborolidine reagent; pyridinium p-toluenesulfonate; tin(IV) chloride; potassium carbonate; Dess-Martin periodane; triphenylphosphine;
palladium diacetate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
4: Sakurai-Hosomi reaction / 5: Dess-Martin oxidation;
DOI:10.1002/anie.200500029
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: n-BuLi / tetrahydrofuran / -78 °C
1.2: 83 percent / tetrahydrofuran / -78 - 0 °C
2.1: 99 percent / Et3N / CH2Cl2 / 20 °C
3.1: 87 percent / DDQ / CH2Cl2 / 20 °C / pH 7
4.1: Dess-Martin periodinane
5.1: PPh3 / CH2Cl2 / 0 °C
6.1: 86 percent / PPh3 / Pd(OAc)2 / tetrahydrofuran / 50 °C
7.1: 99 percent / PPTS / tetrahydrofuran; acetonitrile / 20 °C
8.1: 86 percent / SnCl4 / CH2Cl2 / -78 °C
9.1: 86 percent / Dess-Martin periodinane
10.1: 92 percent / BH3*THF; (R)-Corey-Bakshi-Shibata oxazaborolidine reagent / tetrahydrofuran / -40 °C
11.1: 95 percent / imidazole / dimethylformamide / 20 °C
12.1: 93 percent / K2CO3 / methanol; tetrahydrofuran / 20 °C
With
1H-imidazole; n-butyllithium; borane-THF; (R)-Corey-Bakshi-Shibata oxazaborolidine reagent; pyridinium p-toluenesulfonate; tin(IV) chloride; potassium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
palladium diacetate;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
4.1: Dess-Martin oxidation / 8.1: Sakurai-Hosomi reaction / 9.1: Dess-Martin oxidation;
DOI:10.1002/anie.200500029
