Technology Process of Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-13,13-dimethoxy-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-11-triphenylsilanyloxy-tridec-3-enyl ester
There total 34 articles about Acetic acid (Z)-(1S,8S,9S,10R,11R)-9-(tert-butyl-dimethyl-silanyloxy)-13,13-dimethoxy-8,10,12,12-tetramethyl-1-[(E)-1-methyl-2-(2-methyl-thiazol-4-yl)-vinyl]-11-triphenylsilanyloxy-tridec-3-enyl ester which
guide to synthetic route it.
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synthetic route:
- Guidance literature:
-
C39H58O4Si2;
With
9-bora-bicyclo[3.3.1]nonane;
In
tetrahydrofuran;
at 20 ℃;
for 4h;
(1E,3S,5Z)-2-methyl-6-iodo-1-(2-methyl-1,3-thiazol-4-yl)-1,5-hexadien-3-yl acetate;
With
triphenyl-arsane; water; caesium carbonate;
(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride;
In
tetrahydrofuran; N,N-dimethyl-formamide;
at 20 ℃;
for 2h;
DOI:10.1021/ja971946k
- Guidance literature:
-
Multi-step reaction with 8 steps
1.1: diethyl ether / 0 - 20 °C
2.1: 93 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetra-n-propylammonium perruthenate / CH2Cl2 / 0 - 20 °C
3.1: n-BuLi / tetrahydrofuran / -78 °C
3.2: 97 percent / tetrahydrofuran / -78 - 20 °C
4.1: 64 percent / N-iodosuccinimide; AgNO3 / acetone
5.1: 65 percent / dicyclohexylborane; AcOH / diethyl ether
6.1: 86 percent / PhSH; BF3*OEt2 / CH2Cl2 / 20 °C
7.1: 99 percent / pyridine; 4-DMAP / CH2Cl2 / 20 °C
8.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C
8.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C
With
pyridine; dmap; N-iodo-succinimide; n-butyllithium; 4 A molecular sieve; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; silver nitrate; acetic acid; thiophenol; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane;
tetrapropylammonium perruthennate;
In
tetrahydrofuran; diethyl ether; dichloromethane; acetone;
1.1: Grignard reaction / 2.1: Oxidation / 3.1: Metallation / 3.2: Emmons reaction / 4.1: iododesilylation / 5.1: Reduction / 6.1: dealkylation / 7.1: Acetylation / 8.1: hydroboration / 8.2: Suzuki coupling;
DOI:10.1021/ja971946k
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 95 percent / pyridinium p-toluenesulfonate / methanol / 20 °C
2.1: (COCl)2; DMSO / CH2Cl2 / -78 °C
2.2: Et3N / CH2Cl2 / -78 - 20 °C
3.1: diethyl ether / 0 - 20 °C
4.1: 93 percent / N-methylmorpholine N-oxide; 4 Angstroem molecular sieves / tetra-n-propylammonium perruthenate / CH2Cl2 / 0 - 20 °C
5.1: n-BuLi / tetrahydrofuran / -78 °C
5.2: 97 percent / tetrahydrofuran / -78 - 20 °C
6.1: 64 percent / N-iodosuccinimide; AgNO3 / acetone
7.1: 65 percent / dicyclohexylborane; AcOH / diethyl ether
8.1: 86 percent / PhSH; BF3*OEt2 / CH2Cl2 / 20 °C
9.1: 99 percent / pyridine; 4-DMAP / CH2Cl2 / 20 °C
10.1: 9-borabicyclo[3.3.1]nonane / tetrahydrofuran / 4 h / 20 °C
10.2: 75 percent / Cs2CO3; Ph3As; H2O / PdCl2(1,1'-bis(diphenylphosphino)ferrocene)2 / dimethylformamide; tetrahydrofuran / 2 h / 20 °C
With
pyridine; dmap; N-iodo-succinimide; n-butyllithium; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; bis(cyclohexanyl)borane; pyridinium p-toluenesulfonate; silver nitrate; acetic acid; dimethyl sulfoxide; thiophenol; 4-methylmorpholine N-oxide; 9-bora-bicyclo[3.3.1]nonane;
tetrapropylammonium perruthennate;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetone;
1.1: methanolysis / 2.1: Condensation / 2.2: Elimination / 3.1: Grignard reaction / 4.1: Oxidation / 5.1: Metallation / 5.2: Emmons reaction / 6.1: iododesilylation / 7.1: Reduction / 8.1: dealkylation / 9.1: Acetylation / 10.1: hydroboration / 10.2: Suzuki coupling;
DOI:10.1021/ja971946k
