Technology Process of (8E,12E,14E)-(3S,4R,5R,10R,16S,17R)-3,4-Bis-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-8,10,12,14,16-pentamethyl-17-((S)-1-methyl-undecyl)-1,6-dioxa-cycloheptadeca-8,12,14-triene-2,7,11-trione
There total 13 articles about (8E,12E,14E)-(3S,4R,5R,10R,16S,17R)-3,4-Bis-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-8,10,12,14,16-pentamethyl-17-((S)-1-methyl-undecyl)-1,6-dioxa-cycloheptadeca-8,12,14-triene-2,7,11-trione 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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637741-49-2
(8E,12E,14E)-(3S,4R,5R,10R,11R,16S,17R)-11-Hydroxy-3,4-bis-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-8,10,12,14,16-pentamethyl-17-((S)-1-methyl-undecyl)-1,6-dioxa-cycloheptadeca-8,12,14-triene-2,7-dione
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637741-50-5
(8E,12E,14E)-(3S,4R,5R,10R,16S,17R)-3,4-Bis-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-8,10,12,14,16-pentamethyl-17-((S)-1-methyl-undecyl)-1,6-dioxa-cycloheptadeca-8,12,14-triene-2,7,11-trione
- Guidance literature:
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With
pyridine; Dess-Martin periodane;
In
dichloromethane;
at 20 ℃;
for 0.5h;
DOI:10.1039/b305818b
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637741-50-5
(8E,12E,14E)-(3S,4R,5R,10R,16S,17R)-3,4-Bis-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-8,10,12,14,16-pentamethyl-17-((S)-1-methyl-undecyl)-1,6-dioxa-cycloheptadeca-8,12,14-triene-2,7,11-trione
- Guidance literature:
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Multi-step reaction with 11 steps
1.1: manganese dioxide / CH2Cl2 / 12 h / 20 °C
2.1: 1.27 g / sodium chlorite; sodium dihydrogenphosphate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 20 h / 20 °C
3.1: 79 percent / N,N-dimethylaminopyridine; dicyclohexylcarbodiimide; N,N-dimethylaminopyridine hydrogenchloride / CH2Cl2 / 6 h / Heating
4.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C
4.2: K3PO4 / PdCl2(dppf) / tetrahydrofuran; dimethylformamide; H2O / 0.5 h / 65 °C
5.1: 692 mg / aq. hydrogen fluoride / acetonitrile / 3 h / -10 °C
6.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 3 h / 20 °C
7.1: 462 mg / sodium chlorite; sodium dihydrogenphosphate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 20 h / 20 °C
8.1: 48 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.17 h / -78 °C
9.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C
9.2: 40 percent / 4-dimethylaminopyridine / tetrahydrofuran; toluene / 15 h / Heating
10.1: 54 percent / aq. hydrogen fluoride / acetonitrile / 10 h / 0 °C
11.1: 93 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 0.5 h / 20 °C
With
pyridine; dmap; manganese(IV) oxide; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; N,N-dimethylaminopyridine hydrogenchloride; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide;
In
tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol;
3.1: Keck's esterification / 4.1: Suzuki-Miyaura coupling;
DOI:10.1039/b305818b
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637741-50-5
(8E,12E,14E)-(3S,4R,5R,10R,16S,17R)-3,4-Bis-(4-methoxy-benzyloxy)-5-(4-methoxy-benzyloxymethyl)-8,10,12,14,16-pentamethyl-17-((S)-1-methyl-undecyl)-1,6-dioxa-cycloheptadeca-8,12,14-triene-2,7,11-trione
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: trifluoroacetic acid / CH2Cl2 / 1 h / 0 °C
2.1: pyridine / CH2Cl2 / 3 h / 20 °C
2.2: 938 mg / 4-dimethylaminopyridine / CH2Cl2 / 1 h / 20 °C
3.1: 9-BBN / tetrahydrofuran / 12 h / 20 °C
3.2: K3PO4 / PdCl2(dppf) / tetrahydrofuran; dimethylformamide; H2O / 0.5 h / 65 °C
4.1: 692 mg / aq. hydrogen fluoride / acetonitrile / 3 h / -10 °C
5.1: Dess-Martin periodinane; pyridine / CH2Cl2 / 3 h / 20 °C
6.1: 462 mg / sodium chlorite; sodium dihydrogenphosphate; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 20 h / 20 °C
7.1: 48 percent / diisobutylaluminum hydride / CH2Cl2; hexane / 0.17 h / -78 °C
8.1: triethylamine; 2,4,6-trichlorobenzoyl chloride / tetrahydrofuran / 2 h / 20 °C
8.2: 40 percent / 4-dimethylaminopyridine / tetrahydrofuran; toluene / 15 h / Heating
9.1: 54 percent / aq. hydrogen fluoride / acetonitrile / 10 h / 0 °C
10.1: 93 percent / Dess-Martin periodinane; pyridine / CH2Cl2 / 0.5 h / 20 °C
With
pyridine; sodium chlorite; sodium dihydrogenphosphate; 9-borabicyclo[3.3.1]nonane dimer; 2-methyl-but-2-ene; 2,4,6-trichlorobenzoyl chloride; hydrogen fluoride; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; trifluoroacetic acid;
In
tetrahydrofuran; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol;
3.1: Suzuki-Miyaura coupling;
DOI:10.1039/b305818b