(4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-10-(methoxymethoxy)-12-methyl-4-(methylsulfonyloxy)tridec-6-enyl pivalate

Base Information

Chemical Name:(4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-10-(methoxymethoxy)-12-methyl-4-(methylsulfonyloxy)tridec-6-enyl pivalate
CAS No.:1417995-93-7
Molecular Formula:C₃₈H₆₀O₈SSi
Molecular Weight:705.041
Hs Code.:

Synonyms:(4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-10-(methoxymethoxy)-12-methyl-4-(methylsulfonyloxy)tridec-6-enyl pivalate

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Chemical Property of (4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-10-(methoxymethoxy)-12-methyl-4-(methylsulfonyloxy)tridec-6-enyl pivalate

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Technology Process of (4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-10-(methoxymethoxy)-12-methyl-4-(methylsulfonyloxy)tridec-6-enyl pivalate

There total 18 articles about (4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-10-(methoxymethoxy)-12-methyl-4-(methylsulfonyloxy)tridec-6-enyl pivalate 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:

Reference yield: 100.0%

: 1417996-07-6
(4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-4-hydroxy-10-(methoxymethoxy)-12-methyltridec-6-enyl pivalate

: 124-63-0
methanesulfonyl chloride

: 1417995-93-7
(4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-10-(methoxymethoxy)-12-methyl-4-(methylsulfonyloxy)tridec-6-enyl pivalate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h; Inert atmosphere;
DOI:10.1002/ejoc.201201119

Reference yield:

: 1417995-97-1
(R)-4-benzyl-3-[(S)-4-(methoxymethoxy)hept-6-enoyl]oxazolidin-2-one

: 1417995-93-7
(4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-10-(methoxymethoxy)-12-methyl-4-(methylsulfonyloxy)tridec-6-enyl pivalate

Guidance literature:: Multi-step reaction with 8 steps

1.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

1.2: 3.5 h / -75 °C / Inert atmosphere

2.1: sodium tetrahydroborate / tetrahydrofuran; water / 1 h / 0 - 20 °C / Inert atmosphere

3.1: 1H-imidazole / dichloromethane / 0.5 h / -20 °C / Inert atmosphere

4.1: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Inert atmosphere

4.2: 2 h / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

6.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / -78 °C / Inert atmosphere

6.2: Julia-Kocienski Olefination / -78 °C / Inert atmosphere

7.1: pyridinium p-toluenesulfonate / ethanol / 6 h / 55 °C / Inert atmosphere

8.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; dimethylsulfide borane complex; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; Dess-Martin periodane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; 6.1: |Julia-Kocienski Olefination;
DOI:10.1002/ejoc.201201119

Reference yield:

: 1258958-40-5
(4S)-4-(methoxymethoxy)hept-6-enoic acid

: 1417995-93-7
(4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-10-(methoxymethoxy)-12-methyl-4-(methylsulfonyloxy)tridec-6-enyl pivalate

Guidance literature:: Multi-step reaction with 9 steps

1.1: triethylamine; pivaloyl chloride / tetrahydrofuran / -20 °C / Inert atmosphere

1.2: 0.5 h / -20 °C / Inert atmosphere

1.3: -20 - 20 °C / Inert atmosphere

2.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 3.5 h / -75 °C / Inert atmosphere

3.1: sodium tetrahydroborate / tetrahydrofuran; water / 1 h / 0 - 20 °C / Inert atmosphere

4.1: 1H-imidazole / dichloromethane / 0.5 h / -20 °C / Inert atmosphere

5.1: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Inert atmosphere

5.2: 2 h / Inert atmosphere

6.1: Dess-Martin periodane / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

7.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / -78 °C / Inert atmosphere

7.2: Julia-Kocienski Olefination / -78 °C / Inert atmosphere

8.1: pyridinium p-toluenesulfonate / ethanol / 6 h / 55 °C / Inert atmosphere

9.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium tetrahydroborate; dimethylsulfide borane complex; pyridinium p-toluenesulfonate; pivaloyl chloride; potassium hexamethylsilazane; Dess-Martin periodane; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; 7.1: |Julia-Kocienski Olefination;
DOI:10.1002/ejoc.201201119