Technology Process of (2S,4S,7S,8R,9S,10S,11R)-4-(tert-butyldimethylsilyloxy)-1-((4-methoxyphenyl)oxy)-7-hydroxy-2,8,10,12-tetramethyl-9,11-[(bis-dimethylmethylene)dioxy]-tridec-12-en-5-one
There total 17 articles about (2S,4S,7S,8R,9S,10S,11R)-4-(tert-butyldimethylsilyloxy)-1-((4-methoxyphenyl)oxy)-7-hydroxy-2,8,10,12-tetramethyl-9,11-[(bis-dimethylmethylene)dioxy]-tridec-12-en-5-one 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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1415730-34-5
(2S,4S,7S,8R,9S,10S,11R)-4-(tert-butyldimethylsilyloxy)-1-((4-methoxyphenyl)oxy)-7-hydroxy-2,8,10,12-tetramethyl-9,11-[(bis-dimethylmethylene)dioxy]-tridec-12-en-5-one
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1415730-28-7
(2S,4S,7R,8R,9S,10S,11R)-4-(tert-butyldimethylsilyloxy)-1-((4-methoxyphenyl)oxy)-7-hydroxy-2,8,10,12-tetramethyl-9,11-[(bis-dimethylmethylene)dioxy]-tridec-12-en-5-one
- Guidance literature:
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Multi-step reaction with 5 steps
1.1: pyridine; pyridine hydrogenfluoride; water / tetrahydrofuran / 120 h / 20 °C / Inert atmosphere
2.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere
3.1: lithium borohydride; ethanol / diethyl ether / 4 h / -10 °C / Inert atmosphere
4.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
4.2: 1 h / -78 - 0 °C / Inert atmosphere
5.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
5.2: 5 h / -78 °C / Inert atmosphere
With
pyridine; lithium borohydride; oxalyl dichloride; ethanol; water; pyridinium p-toluenesulfonate; pyridine hydrogenfluoride; dimethyl sulfoxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/j.tet.2012.10.008
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1415730-34-5
(2S,4S,7S,8R,9S,10S,11R)-4-(tert-butyldimethylsilyloxy)-1-((4-methoxyphenyl)oxy)-7-hydroxy-2,8,10,12-tetramethyl-9,11-[(bis-dimethylmethylene)dioxy]-tridec-12-en-5-one
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1415730-28-7
(2S,4S,7R,8R,9S,10S,11R)-4-(tert-butyldimethylsilyloxy)-1-((4-methoxyphenyl)oxy)-7-hydroxy-2,8,10,12-tetramethyl-9,11-[(bis-dimethylmethylene)dioxy]-tridec-12-en-5-one
- Guidance literature:
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Multi-step reaction with 6 steps
1.1: tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
2.1: phthalic acid dimethyl ester; water / dichloromethane / 4 h / 20 °C / Inert atmosphere
3.1: (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; dimethyl sulfide borane / tetrahydrofuran; toluene / 2 h / -30 °C / Inert atmosphere
4.1: 2,6-dimethylpyridine / dichloromethane / 7.5 h / -78 °C / Inert atmosphere
5.1: pyridinium p-toluenesulfonate; mercury(II) diacetate / tetrahydrofuran / 5 h / 45 °C / pH 7 / Inert atmosphere
6.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
6.2: 5 h / -78 °C / Inert atmosphere
With
2,6-dimethylpyridine; phthalic acid dimethyl ester; mercury(II) diacetate; water; dimethyl sulfide borane; pyridinium p-toluenesulfonate; lithium hexamethyldisilazane; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole;
In
tetrahydrofuran; dichloromethane; toluene;
1.1: |Grignard Reaction;
DOI:10.1016/j.tet.2012.10.008
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1415730-34-5
(2S,4S,7S,8R,9S,10S,11R)-4-(tert-butyldimethylsilyloxy)-1-((4-methoxyphenyl)oxy)-7-hydroxy-2,8,10,12-tetramethyl-9,11-[(bis-dimethylmethylene)dioxy]-tridec-12-en-5-one
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1415730-28-7
(2S,4S,7R,8R,9S,10S,11R)-4-(tert-butyldimethylsilyloxy)-1-((4-methoxyphenyl)oxy)-7-hydroxy-2,8,10,12-tetramethyl-9,11-[(bis-dimethylmethylene)dioxy]-tridec-12-en-5-one
- Guidance literature:
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Multi-step reaction with 7 steps
1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
1.2: 1 h / -78 - 0 °C / Inert atmosphere
2.1: di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 °C / Inert atmosphere
2.2: 0.5 h / 0 °C / Inert atmosphere
2.3: 4.5 h / -78 - 0 °C / Inert atmosphere
3.1: pyridine; pyridine hydrogenfluoride; water / tetrahydrofuran / 120 h / 20 °C / Inert atmosphere
4.1: pyridinium p-toluenesulfonate / dichloromethane / 3 h / 20 °C / Inert atmosphere
5.1: lithium borohydride; ethanol / diethyl ether / 4 h / -10 °C / Inert atmosphere
6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C / Inert atmosphere
6.2: 1 h / -78 - 0 °C / Inert atmosphere
7.1: lithium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
7.2: 5 h / -78 °C / Inert atmosphere
With
pyridine; lithium borohydride; oxalyl dichloride; ethanol; di-n-butylboryl trifluoromethanesulfonate; water; pyridinium p-toluenesulfonate; pyridine hydrogenfluoride; dimethyl sulfoxide; lithium hexamethyldisilazane;
In
tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1016/j.tet.2012.10.008