Technology Process of methyl (5R,7R,9E,11Z,13S,14R,16E)-5,7-bis(tert-butyldimethylsilyloxy)-18-(methoxycarbonyl)oxy-13-[(4-methoxyphenyl)methoxy]-14-methyl-3-oxo-9,11,16-octadecatriene-1-carboxylate
There total 13 articles about methyl (5R,7R,9E,11Z,13S,14R,16E)-5,7-bis(tert-butyldimethylsilyloxy)-18-(methoxycarbonyl)oxy-13-[(4-methoxyphenyl)methoxy]-14-methyl-3-oxo-9,11,16-octadecatriene-1-carboxylate 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:
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![(2E,5R,6S,7Z,9E,12R,14R)-12,14-bis(tert-butyldimethylsilyloxy)-15-(2,2-dimethyl-1,3-dioxin-4-one-6-yl)-1-(methoxycarbonyl)oxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-2,7,9-pentadecatriene](/Databaselist/images/loading.webp)
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640270-71-9
(2E,5R,6S,7Z,9E,12R,14R)-12,14-bis(tert-butyldimethylsilyloxy)-15-(2,2-dimethyl-1,3-dioxin-4-one-6-yl)-1-(methoxycarbonyl)oxy-6-[(4-methoxyphenyl)methoxy]-5-methyl-2,7,9-pentadecatriene
- Guidance literature:
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In
methanol; toluene;
at 110 ℃;
for 3h;
DOI:10.1021/ja038732p
DOI:10.1021/ja048320w
- Guidance literature:
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Multi-step reaction with 13 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: 93 percent / imidazole / dimethylformamide / 5 h / 0 °C
8.1: 97 percent / NBS; AgNO3 / acetone / 0.5 h / 20 °C
9.1: Pd2(dba)3; PPh3; Bu3SnH / tetrahydrofuran / 2 h
9.2: 84 percent / I2 / CH2Cl2 / 1 h / 0 °C
10.1: 97 percent / CuCl; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 2 h
11.1: 94 percent / NH4F / methanol / 24 h / 0 °C
12.1: 100 percent / pyridine / CH2Cl2 / 2 h / 0 °C
13.1: 98 percent / toluene; methanol / 3 h / 110 °C
With
pyridine; 1H-imidazole; ammonium fluoride; sodium tetrahydroborate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium(0); tris(dibenzylideneacetone)dipalladium (0); diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; silver nitrate; triphenylphosphine; copper(l) chloride;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
3.1: Mukaiyama aldol reaction / 4.1: Dess-Martin oxidation / 6.1: Prasad's procedure / 10.1: Stille coupling;
DOI:10.1021/ja048320w
- Guidance literature:
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Multi-step reaction with 12 steps
1.1: 100 percent / DIBAL-H / toluene / 2 h / -52 °C
2.1: BF3*Et2O / CH2Cl2 / 0.75 h / -78 °C
3.1: Dess-Martin periodinane / CH2Cl2 / 6.5 h / 0 °C
4.1: 7.95 g / aq. HF / acetonitrile / 8 h / 20 °C
5.1: 100 percent / Et2BOMe; NaBH4 / tetrahydrofuran; methanol / 8 h / -78 °C
6.1: 93 percent / imidazole / dimethylformamide / 5 h / 0 °C
7.1: 97 percent / NBS; AgNO3 / acetone / 0.5 h / 20 °C
8.1: Pd2(dba)3; PPh3; Bu3SnH / tetrahydrofuran / 2 h
8.2: 84 percent / I2 / CH2Cl2 / 1 h / 0 °C
9.1: 97 percent / CuCl; Pd(PPh3)4 / dimethylsulfoxide; tetrahydrofuran / 2 h
10.1: 94 percent / NH4F / methanol / 24 h / 0 °C
11.1: 100 percent / pyridine / CH2Cl2 / 2 h / 0 °C
12.1: 98 percent / toluene; methanol / 3 h / 110 °C
With
pyridine; 1H-imidazole; ammonium fluoride; sodium tetrahydroborate; N-Bromosuccinimide; tetrakis(triphenylphosphine) palladium(0); tris(dibenzylideneacetone)dipalladium (0); diethyl methoxy borane; boron trifluoride diethyl etherate; hydrogen fluoride; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; silver nitrate; triphenylphosphine; copper(l) chloride;
In
tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; acetone; toluene; acetonitrile;
2.1: Mukaiyama aldol reaction / 3.1: Dess-Martin oxidation / 5.1: Prasad's procedure / 9.1: Stille coupling;
DOI:10.1021/ja048320w
