Technology Process of (2E,4Z,6S,7R,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-triene
There total 20 articles about (2E,4Z,6S,7R,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-triene 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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1402167-43-4
(2E,4Z,6S,7R,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-15-(3',6'-diisopropoxy-2'-methoxyphenyl)-6,12-dimethoxy-2,8,10,14-tetramethyl-pentadeca-2,4,8-triene
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1402167-44-5
(2E,4Z,6S,7R,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-triene
- Guidance literature:
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With
copper(II) nitrate;
In
acetic anhydride;
at 0 ℃;
for 2.25h;
regioselective reaction;
DOI:10.1002/chem.201201600
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1402167-44-5
(2E,4Z,6S,7R,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-triene
- Guidance literature:
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Multi-step reaction with 8 steps
1: potassium hydride / tetrahydrofuran; mineral oil / 16 h / 0 - 20 °C
2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / dichloromethane; water / 16 h / 20 °C
3: sodium periodate / water; acetone / 1 h / 20 °C
4: samarium diiodide / tetrahydrofuran / 1 h / -78 °C
5: Martins sulfurane / dichloromethane / 1 h / 0 °C
6: L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
7: 1H-imidazole / N,N-dimethyl-formamide / 16 h
8: copper(II) nitrate / acetic anhydride / 2.25 h / 0 °C
With
1H-imidazole; sodium periodate; osmium(VIII) oxide; samarium diiodide; Martins sulfurane; potassium hydride; L-Selectride; copper(II) nitrate; 4-methylmorpholine N-oxide;
In
tetrahydrofuran; dichloromethane; water; acetic anhydride; N,N-dimethyl-formamide; acetone; mineral oil;
4: Reformatsky-type reaction;
DOI:10.1002/chem.201201600
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1402167-44-5
(2E,4Z,6S,7R,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-1-(tert-butyldiphenylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-triene
- Guidance literature:
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Multi-step reaction with 12 steps
1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 2 h / -20 °C
2.1: diisobutylaluminium hydride / tetrahydrofuran; cyclohexane / 3 h / -78 - -20 °C
3.1: 1H-imidazole / dichloromethane / 0.25 h / -20 °C
4.1: camphor-10-sulfonic acid / methanol; dichloromethane / 2 h / 0 °C
5.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / 85 °C
6.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / -78 °C
6.2: 2 h / -78 °C
7.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 20 °C
8.1: samarium diiodide / tetrahydrofuran / 1.5 h / -78 °C
9.1: Martins sulfurane / dichloromethane / 1 h / 0 °C
10.1: L-Selectride / tetrahydrofuran / 0.5 h / -78 °C
11.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h
12.1: copper(II) nitrate / acetic anhydride / 2.25 h / 0 °C
With
1H-imidazole; samarium diiodide; Martins sulfurane; camphor-10-sulfonic acid; isopropylmagnesium chloride; L-Selectride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; copper(II) nitrate; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; cyclohexane; acetic anhydride; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1002/chem.201201600
