(3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-14-(3-(tert-butyldimethylsilyloxy)-2-chlorophenyl)-3-ethyl-5,7-dimethyl-10-oxotetradeca-1,11,13-trien-4-yl acrylate

Base Information

• Chemical Name: (3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-14-(3-(tert-butyldimethylsilyloxy)-2-chlorophenyl)-3-ethyl-5,7-dimethyl-10-oxotetradeca-1,11,13-trien-4-yl acrylate
• CAS No.: 1643478-66-3
• Molecular Formula: C₃₉H₆₃ClO₅Si₂
• Molecular Weight: 703.55

Synonyms:(3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-14-(3-(tert-butyldimethylsilyloxy)-2-chlorophenyl)-3-ethyl-5,7-dimethyl-10-oxotetradeca-1,11,13-trien-4-yl acrylate

Chemical Property of (3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-14-(3-(tert-butyldimethylsilyloxy)-2-chlorophenyl)-3-ethyl-5,7-dimethyl-10-oxotetradeca-1,11,13-trien-4-yl acrylate

Chemical Property:

Purity/Quality:

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• Pictogram(s):  
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Technology Process of (3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-14-(3-(tert-butyldimethylsilyloxy)-2-chlorophenyl)-3-ethyl-5,7-dimethyl-10-oxotetradeca-1,11,13-trien-4-yl acrylate

There total 26 articles about (3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-14-(3-(tert-butyldimethylsilyloxy)-2-chlorophenyl)-3-ethyl-5,7-dimethyl-10-oxotetradeca-1,11,13-trien-4-yl acrylate 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: 85.0%

(1E,3E,7S,8R,10R,11R,12R)-7-(tert-butyldimethylsilyloxy)-1-(3-(tert-butyldimethylsilyloxy)-2-chlorophenyl)-12-ethyl-11-hydroxy-8,10-dimethyltetradeca-1,3,13-trien-5-one (1643478-64-1) + acryloyl chloride (814-68-6,25189-84-8) → (3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-14-(3-(tert-butyldimethylsilyloxy)-2-chlorophenyl)-3-ethyl-5,7-dimethyl-10-oxotetradeca-1,11,13-trien-4-yl acrylate (1643478-66-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1039/c4ob00250d

Reference yield:

(R)-4-((4-methoxybenzyloxy)methyl)hexan-3-one (1643478-23-2) → (3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-14-(3-(tert-butyldimethylsilyloxy)-2-chlorophenyl)-3-ethyl-5,7-dimethyl-10-oxotetradeca-1,11,13-trien-4-yl acrylate (1643478-66-3)

Guidance literature:

Multi-step reaction with 14 steps

1.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 2.5 h / -78 - 0 °C / Inert atmosphere

1.2: 14 h / -78 - -25 °C / Inert atmosphere

2.1: zinc(II) tetrahydroborate / dichloromethane; diethyl ether / 6 h / -40 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / -10 °C / Molecular sieve; Inert atmosphere

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: 0.5 h / -78 °C / Inert atmosphere

4.3: 0.25 h / -78 °C / Inert atmosphere

5.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / 1 h / 120 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -40 °C / Inert atmosphere

7.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0 °C / Inert atmosphere

8.1: sodium hexamethyldisilazane / tetrahydrofuran / 18 h / -78 - 20 °C / Inert atmosphere

9.1: pyridine hydrogenfluoride / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere

10.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 1.5 h / 0 °C / Inert atmosphere

11.1: n-butyllithium / hexane / 0.67 h / -78 °C / Inert atmosphere

11.2: 1 h / Inert atmosphere

11.3: Inert atmosphere

12.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 1 h / 0 - 20 °C / Inert atmosphere

13.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform; aq. phosphate buffer / 1 h / 0 °C / pH 7 / Inert atmosphere

14.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

With n-butyllithium; zinc(II) tetrahydroborate; 2,2'-azobis(isobutyronitrile); dicyclohexylboron chloride; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; diisobutylaluminium hydride; pyridine hydrogenfluoride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; aq. phosphate buffer; diethyl ether; hexane; dichloromethane; chloroform; dimethyl sulfoxide; toluene; 5.1: |Barton-McCombie Deoxygenation / 8.1: |Julia-Kocienski Olefination / 10.1: |Parikh-Doering Oxidation;

DOI:10.1039/c4ob00250d

Reference yield:

C14H22O2 → (3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-14-(3-(tert-butyldimethylsilyloxy)-2-chlorophenyl)-3-ethyl-5,7-dimethyl-10-oxotetradeca-1,11,13-trien-4-yl acrylate (1643478-66-3)

Guidance literature:

Multi-step reaction with 17 steps

1.1: palladium on activated charcoal; hydrogen / 20 °C / 760.05 Torr

2.1: sodium hydride / N,N-dimethyl-formamide / Inert atmosphere; Heating

2.2: Inert atmosphere

3.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere

4.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 2.5 h / -78 - 0 °C / Inert atmosphere

4.2: 14 h / -78 - -25 °C / Inert atmosphere

5.1: zinc(II) tetrahydroborate / dichloromethane; diethyl ether / 6 h / -40 °C

6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / -10 °C / Molecular sieve; Inert atmosphere

7.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

7.2: 0.5 h / -78 °C / Inert atmosphere

7.3: 0.25 h / -78 °C / Inert atmosphere

8.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / 1 h / 120 °C / Inert atmosphere

9.1: diisobutylaluminium hydride / dichloromethane; toluene / 2 h / -40 °C / Inert atmosphere

10.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0 °C / Inert atmosphere

11.1: sodium hexamethyldisilazane / tetrahydrofuran / 18 h / -78 - 20 °C / Inert atmosphere

12.1: pyridine hydrogenfluoride / tetrahydrofuran / 20 h / 0 - 20 °C / Inert atmosphere

13.1: triethylamine; sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 1.5 h / 0 °C / Inert atmosphere

14.1: n-butyllithium / hexane / 0.67 h / -78 °C / Inert atmosphere

14.2: 1 h / Inert atmosphere

14.3: Inert atmosphere

15.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 1 h / 0 - 20 °C / Inert atmosphere

16.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform; aq. phosphate buffer / 1 h / 0 °C / pH 7 / Inert atmosphere

17.1: triethylamine / dichloromethane / 2 h / 0 °C / Inert atmosphere

With n-butyllithium; zinc(II) tetrahydroborate; 2,2'-azobis(isobutyronitrile); palladium on activated charcoal; dicyclohexylboron chloride; hydrogen; tri-n-butyl-tin hydride; sodium hexamethyldisilazane; sulfur trioxide pyridine complex; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; aq. phosphate buffer; diethyl ether; hexane; dichloromethane; chloroform; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 8.1: |Barton-McCombie Deoxygenation / 11.1: |Julia-Kocienski Olefination / 13.1: |Parikh-Doering Oxidation;

DOI:10.1039/c4ob00250d

upstream raw materials:

C₃₄H₆₄O₄Si₂

(3S,4R,6R,7R,8R)-3-(tert-butyldimethylsilyloxy)-8-ethyl-7-(4-methoxybenzyloxy)-4,6-dimethyldec-9-en-1-ol

C₂₈H₄₈O₄Si

2-<(benzyloxy)-methyl>butyraldehyde

Downstream raw materials:

(5R,6R)-6-((2R,4R,5S,8E,10E)-5-(tert-butyldimethylsilyloxy)-11-(3-(tert-butyldimethylsilyloxy)-2-chlorophenyl)-4-methyl-7-oxoundeca-8,10-dien-2-yl)-5-ethyl-5,6-dihydro-2H-pyran-2-one

(5R,6R)-6-((2R,4R,5S,8E,10E)-11-(2-chloro-3-hydroxyphenyl)-5-hydroxy-4-methyl-7-oxoundeca-8,10-dien-2-yl)-5-ethyl-5,6-dihydro-2H-pyran-2-one

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