Technology Process of (2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-(tert-butyldimethylsilyloxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienamide
There total 46 articles about (2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-(tert-butyldimethylsilyloxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienamide 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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869732-33-2
(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid
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869732-09-2
(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienamide
- Guidance literature:
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(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-((tert-butyldimethylsilyl)oxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienoic acid;
With
pyridine; di-tert-butyl dicarbonate;
In
1,4-dioxane;
for 0.25h;
Inert atmosphere;
With
ammonium bicarbonate;
In
1,4-dioxane;
at 20 ℃;
for 18h;
Inert atmosphere;
DOI:10.1016/j.tet.2014.03.020
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869732-09-2
(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-(tert-butyldimethylsilyloxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienamide
- Guidance literature:
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Multi-step reaction with 10 steps
1.1: 99 percent / 1H-imidazole / dimethylformamide / 0 - 20 °C
2.1: DIBAL-H / toluene / 2 h / -78 °C
3.1: 19.8 g / benzene / 2 h / Heating
4.1: 95 percent / 4 Angstroem molecular sieves; Proton-Sponge / CH2Cl2 / 3 h / 20 °C
5.1: 99 percent / HCl / methanol / 1 h / 20 °C
6.1: 99 percent / oxalyl chloride; DMSO; Et3N / CH2Cl2 / 4 h / 20 °C
7.1: Cp2ZrHCl / toluene / 6 h / 50 °C
7.2: ZnMe2 / toluene / -65 - 0 °C
7.3: 55 percent / toluene / 1 h / 0 °C
8.1: 87 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
9.1: aq. LiOH / tetrahydrofuran; methanol / 48 h
10.1: ethyl chloroformate; Et3N / CH2Cl2 / 0.5 h / -20 °C
10.2: 10.0 mg / NH3 (gas) / CH2Cl2 / -20 °C
With
1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; Schwartz's reagent; oxalyl dichloride; 4 A molecular sieve; Proton-Sponge; chloroformic acid ethyl ester; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene;
6.1: Swern oxidation;
DOI:10.1021/ja055384d
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869732-09-2
(2E,6S,7S,8E,10S,11R,12S,14R)-15-(3-(benzyloxy)-5-bromo-2-methoxyphenyl)-7-(tert-butyldimethylsilyloxy)-6,12-dimethoxy-11-(methoxymethoxy)-2,8,10,14-tetramethylpentadeca-2,8-dienamide
- Guidance literature:
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Multi-step reaction with 4 steps
1.1: Cp2ZrHCl / toluene / 6 h / 50 °C
1.2: ZnMe2 / toluene / -65 - 0 °C
1.3: 55 percent / toluene / 1 h / 0 °C
2.1: 87 percent / 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
3.1: aq. LiOH / tetrahydrofuran; methanol / 48 h
4.1: ethyl chloroformate; Et3N / CH2Cl2 / 0.5 h / -20 °C
4.2: 10.0 mg / NH3 (gas) / CH2Cl2 / -20 °C
With
2,6-dimethylpyridine; lithium hydroxide; Schwartz's reagent; chloroformic acid ethyl ester; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1021/ja055384d
