Technology Process of (2E,5R,6S,7Z,9E,12R)-12-(tert-butyldimethylsilyloxy)-13-[(6R)-4-methoxymethoxy-5,6-dihydropyran-2-one-6-yl]-6-[(4-methoxyphenyl)methoxy]-5-methyl-2,7,9-tridecatrien-1-ol
There total 12 articles about (2E,5R,6S,7Z,9E,12R)-12-(tert-butyldimethylsilyloxy)-13-[(6R)-4-methoxymethoxy-5,6-dihydropyran-2-one-6-yl]-6-[(4-methoxyphenyl)methoxy]-5-methyl-2,7,9-tridecatrien-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
pyridine hydrogenfluoride;
In
tetrahydrofuran;
at 0 ℃;
for 12h;
DOI:10.1021/ja048320w
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 5.62 g / imidazole / dimethylformamide / 13.5 h / 0 °C
2.1: 100 percent / DIBAL-H / toluene / 2 h / -52 °C
3.1: BF3*Et2O / CH2Cl2 / 0.75 h / -78 °C
4.1: Dess-Martin periodinane / CH2Cl2 / 6.5 h / 0 °C
5.1: 7.95 g / aq. HF / acetonitrile / 8 h / 20 °C
6.1: 100 percent / Et2BOMe; NaBH4 / tetrahydrofuran; methanol / 8 h / -78 °C
7.1: aq. Zn(NO3)2; K2CO3 / methanol / 105 h / 0 °C
8.1: 143 mg / Et3N / CH2Cl2 / 0.5 h / -18 °C
9.1: 89 percent / imidazole / dimethylformamide / 11 h / 0 °C
10.1: Bu3SnH; azobisisobutyronitrile / benzene / 46 h / Heating
10.2: 697 mg / I2 / CH2Cl2 / 0.5 h / 0 °C
11.1: CuCl; PdCl2(MeCN)2 / dimethylsulfoxide / 10 h
12.1: 356 mg / HF*pyridine / tetrahydrofuran / 12 h / 0 °C
With
1H-imidazole; dichloro bis(acetonitrile) palladium(II); zinc(II) nitrate; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; copper(l) chloride;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; acetonitrile; benzene;
3.1: Mukaiyama aldol reaction / 4.1: Dess-Martin oxidation / 6.1: Prasad's procedure / 11.1: Stille coupling;
DOI:10.1021/ja048320w
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: BF3*Et2O / CH2Cl2 / 0.75 h / -78 °C
2.1: Dess-Martin periodinane / CH2Cl2 / 6.5 h / 0 °C
3.1: 7.95 g / aq. HF / acetonitrile / 8 h / 20 °C
4.1: 100 percent / Et2BOMe; NaBH4 / tetrahydrofuran; methanol / 8 h / -78 °C
5.1: aq. Zn(NO3)2; K2CO3 / methanol / 105 h / 0 °C
6.1: 143 mg / Et3N / CH2Cl2 / 0.5 h / -18 °C
7.1: 89 percent / imidazole / dimethylformamide / 11 h / 0 °C
8.1: Bu3SnH; azobisisobutyronitrile / benzene / 46 h / Heating
8.2: 697 mg / I2 / CH2Cl2 / 0.5 h / 0 °C
9.1: CuCl; PdCl2(MeCN)2 / dimethylsulfoxide / 10 h
10.1: 356 mg / HF*pyridine / tetrahydrofuran / 12 h / 0 °C
With
1H-imidazole; dichloro bis(acetonitrile) palladium(II); zinc(II) nitrate; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; potassium carbonate; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; copper(l) chloride;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; benzene;
1.1: Mukaiyama aldol reaction / 2.1: Dess-Martin oxidation / 4.1: Prasad's procedure / 9.1: Stille coupling;
DOI:10.1021/ja048320w
![(2E,5R,6S,7Z,9E,12R)-12-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-13-[(6R)-4-methoxymethoxy-5,6-dihydropyran-2-one-6-yl]-6-[(4-methoxyphenyl)methoxy]-5-methyl-2,7,9-tridecatriene](/Databaselist/images/loading.webp)
