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

Base Information

• Chemical Name: (4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-4-hydroxy-10-(methoxymethoxy)-12-methyltridec-6-enyl pivalate
• CAS No.: 1417996-07-6
• Molecular Formula: C₃₇H₅₈O₆Si
• Molecular Weight: 626.949

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

Chemical Property of (4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-4-hydroxy-10-(methoxymethoxy)-12-methyltridec-6-enyl pivalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-4-hydroxy-10-(methoxymethoxy)-12-methyltridec-6-enyl pivalate

There total 17 articles about (4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-4-hydroxy-10-(methoxymethoxy)-12-methyltridec-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: 70.0%

(4R,10R,12R,E)-4-(tert-butyldimethylsilyloxy)-13-(tert-butyldiphenylsilyloxy)-10-(methoxymethoxy)-12-methyltridec-6-enyl pivalate (1417996-06-5) → (4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-4-hydroxy-10-(methoxymethoxy)-12-methyltridec-6-enyl pivalate (1417996-07-6)

Guidance literature:

With pyridinium p-toluenesulfonate; In ethanol; at 55 ℃; for 6h; Inert atmosphere;

DOI:10.1002/ejoc.201201119

Reference yield:

(4S)-4-(methoxymethoxy)hept-6-enoic acid (1258958-40-5) → (4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-4-hydroxy-10-(methoxymethoxy)-12-methyltridec-6-enyl pivalate (1417996-07-6)

Guidance literature:

Multi-step reaction with 8 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

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

Reference yield:

(R)-4-benzyl-3-[(2R,4R)-4-(methoxymethoxy)-2-methylhept-6-enoyl]oxazolidin-2-one (1417995-98-2) → (4R,10R,12R,E)-13-(tert-butyldiphenylsilyloxy)-4-hydroxy-10-(methoxymethoxy)-12-methyltridec-6-enyl pivalate (1417996-07-6)

Guidance literature:

Multi-step reaction with 6 steps

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

2.1: 1H-imidazole / dichloromethane / 0.5 h / -20 °C / Inert atmosphere

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

3.2: 2 h / Inert atmosphere

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

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

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

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

With 1H-imidazole; sodium tetrahydroborate; dimethylsulfide borane complex; pyridinium p-toluenesulfonate; potassium hexamethylsilazane; Dess-Martin periodane; In tetrahydrofuran; ethanol; dichloromethane; water; toluene; 5.1: |Julia-Kocienski Olefination;

DOI:10.1002/ejoc.201201119

upstream raw materials:

(4S)-4-(methoxymethoxy)hept-6-enoic acid

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

(R)-4-benzyl-3-[(2R,4R)-4-(methoxymethoxy)-2-methylhept-6-enoyl]oxazolidin-2-one

(S)‐7‐(benzyloxy)hept‐1‐en‐4‐ol

Downstream raw materials:

3-{(2S,4S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-hydroxytetrahydrofuran-2-yl}propyl pivalate

3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-oxotetrahydrofuran-2-yl}propyl pivalate

3-{(2S,5S)-5-[(3R,5R)-6-(tert-butyldiphenylsilyloxy)-3-(methoxymethoxy)-5-methylhexyl]-4-methylenetetrahydrofuran-2-yl}propyl pivalate

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

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