Technology Process of (2E,4Z,6S,7R,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trien-1-ol
There total 21 articles about (2E,4Z,6S,7R,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trien-1-ol 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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1402167-44-5
(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
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1402167-82-1
(2E,4Z,6S,7R,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trien-1-ol
- Guidance literature:
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With
pyridine; pyridine hydrogenfluoride;
In
tetrahydrofuran;
at 20 ℃;
for 12h;
DOI:10.1002/chem.201201600
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1402167-82-1
(2E,4Z,6S,7R,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trien-1-ol
- Guidance literature:
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Multi-step reaction with 9 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
9: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 12 h / 20 °C
With
pyridine; 1H-imidazole; sodium periodate; osmium(VIII) oxide; samarium diiodide; Martins sulfurane; potassium hydride; L-Selectride; copper(II) nitrate; pyridine hydrogenfluoride; 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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1402167-82-1
(2E,4Z,6S,7R,8E,10S,11R,12S,14R)-11-(benzyloxy)-7-(tert-butyldimethylsilyloxy)-15-(2',5'-diisopropoxy-6'-methoxy-3'-nitrophenyl)-6,12-dimethoxy-2,8,10,14-tetramethylpentadeca-2,4,8-trien-1-ol
- Guidance literature:
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Multi-step reaction with 13 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
13.1: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 12 h / 20 °C
With
pyridine; 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; pyridine hydrogenfluoride; 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
