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-trienoic acid
There total 24 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-trienoic acid 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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1402167-83-2
(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-trienal
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1402167-84-3
(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-trienoic acid
- Guidance literature:
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With
potassium dihydrogenphosphate; 2-methyl-but-2-ene; sodium perchlorate;
In
water; tert-butyl alcohol;
at 20 ℃;
for 12h;
DOI:10.1002/chem.201201600
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1402167-84-3
(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-trienoic acid
- Guidance literature:
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Multi-step reaction with 11 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
10: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
11: potassium dihydrogenphosphate; 2-methyl-but-2-ene; sodium perchlorate / water; tert-butyl alcohol / 12 h / 20 °C
With
pyridine; 1H-imidazole; sodium periodate; potassium dihydrogenphosphate; osmium(VIII) oxide; samarium diiodide; 2-methyl-but-2-ene; Martins sulfurane; sodium perchlorate; potassium hydride; L-Selectride; sodium hydrogencarbonate; Dess-Martin periodane; copper(II) nitrate; pyridine hydrogenfluoride; 4-methylmorpholine N-oxide;
In
tetrahydrofuran; dichloromethane; water; acetic anhydride; N,N-dimethyl-formamide; acetone; mineral oil; tert-butyl alcohol;
4: Reformatsky-type reaction;
DOI:10.1002/chem.201201600
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1402167-84-3
(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-trienoic acid
- Guidance literature:
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Multi-step reaction with 15 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
14.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0.5 h / 20 °C
15.1: potassium dihydrogenphosphate; 2-methyl-but-2-ene; sodium perchlorate / water; tert-butyl alcohol / 12 h / 20 °C
With
pyridine; 1H-imidazole; potassium dihydrogenphosphate; samarium diiodide; 2-methyl-but-2-ene; Martins sulfurane; camphor-10-sulfonic acid; sodium perchlorate; 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; water; acetic anhydride; N,N-dimethyl-formamide; acetonitrile; mineral oil; tert-butyl alcohol;
DOI:10.1002/chem.201201600
