Technology Process of (2E,4Z,6S,7S,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 15 articles about (2E,4Z,6S,7S,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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1402167-85-4
(2E,4Z,6S,7S,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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1402167-86-5
(2E,4Z,6S,7S,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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1402167-86-5
(2E,4Z,6S,7S,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 10 steps
1.1: 1H-imidazole / dichloromethane / 0.25 h / -20 °C
2.1: camphor-10-sulfonic acid / methanol; dichloromethane / 2 h / 0 °C
3.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / 85 °C
4.1: isopropylmagnesium chloride / tetrahydrofuran / 0.5 h / -78 °C
4.2: 2 h / -78 °C
5.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 3 h / 20 °C
6.1: samarium diiodide / tetrahydrofuran / 1.5 h / -78 °C
7.1: Martins sulfurane / dichloromethane / 1 h / 0 °C
8.1: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 0.25 h / -30 °C
9.1: 1H-imidazole / N,N-dimethyl-formamide / 16 h
10.1: copper(II) nitrate / acetic anhydride / 2.25 h / 0 °C
With
1H-imidazole; samarium diiodide; Martins sulfurane; dimethylsulfide borane complex; camphor-10-sulfonic acid; isopropylmagnesium chloride; sodium hydrogencarbonate; Dess-Martin periodane; copper(II) nitrate; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; dichloromethane; acetic anhydride; N,N-dimethyl-formamide; toluene; acetonitrile;
DOI:10.1002/chem.201201600
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1402167-86-5
(2E,4Z,6S,7S,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:
-
Multi-step reaction with 10 steps
1: camphor-10-sulfonic acid / methanol; dichloromethane / 2 h / 0 °C
2: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / acetonitrile / 3 h / 85 °C
3: tetrahydrofuran; diethyl ether / 2 h / -78 - 0 °C
4: Dess-Martin periodane / dichloromethane / 3 h / 20 °C
5: phenyltrimethylammonium tribromide / tetrahydrofuran / 16.17 h / 0 °C
6: samarium diiodide / tetrahydrofuran / 1 h / -78 °C
7: Martins sulfurane / dichloromethane / 1 h / 0 °C
8: dimethylsulfide borane complex; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 0.25 h / -30 °C
9: 1H-imidazole / N,N-dimethyl-formamide / 16 h
10: copper(II) nitrate / acetic anhydride / 2.25 h / 0 °C
With
1H-imidazole; samarium diiodide; Martins sulfurane; dimethylsulfide borane complex; camphor-10-sulfonic acid; phenyltrimethylammonium tribromide; Dess-Martin periodane; copper(II) nitrate; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione;
In
tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic anhydride; N,N-dimethyl-formamide; toluene; acetonitrile;
6: Reformatsky-type reaction;
DOI:10.1002/chem.201201600
