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

Base Information

Chemical Name:(3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-3-ethyl-5,7-dimethyl-10-oxo-14-phenyltetradeca-1,11,13-trien-4-yl acrylate
CAS No.:1312543-54-6
Molecular Formula:C₃₃H₅₀O₄Si
Molecular Weight:538.843
Hs Code.:

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

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

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Technology Process of (3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-3-ethyl-5,7-dimethyl-10-oxo-14-phenyltetradeca-1,11,13-trien-4-yl acrylate

There total 33 articles about (3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-3-ethyl-5,7-dimethyl-10-oxo-14-phenyltetradeca-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: 79.0%

: 1312543-55-7
(1E,3E,7S,8R,10R,11R,12R)-7-(tert-butyldimethylsilyloxy)-12-ethyl-11-hydroxy-8,10-dimethyl-1-phenyltetradeca-1,3,13-trien-5-one

: 814-68-6,25189-84-8
acryloyl chloride

: 1312543-54-6
(3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-3-ethyl-5,7-dimethyl-10-oxo-14-phenyltetradeca-1,11,13-trien-4-yl acrylate

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃; for 1h;
DOI:10.1016/j.tetlet.2011.04.008

Reference yield:

: 1312543-70-6
(3S,4R,6R,7R,8R)-3-(tert-butyldimethylsilyloxy)-8-ethyl-7-(4-methoxybenzyloxy)-4,6-dimethyldec-9-en-1-ol

: 1312543-54-6
(3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-3-ethyl-5,7-dimethyl-10-oxo-14-phenyltetradeca-1,11,13-trien-4-yl acrylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.75 h / 0 - 20 °C

2.1: n-butyllithium / -78

2.2: 0.75 h / -78 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 0.17 h / 0 °C / pH 7

4.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C

With n-butyllithium; sulfur trioxide pyridine complex; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; chloroform; -78; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2011.04.008

Reference yield:

: 1312543-69-3
C₃₄H₆₄O₄Si₂

: 1312543-54-6
(3R,4R,5R,7R,8S,11E,13E)-8-(tert-butyldimethylsilyloxy)-3-ethyl-5,7-dimethyl-10-oxo-14-phenyltetradeca-1,11,13-trien-4-yl acrylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine hydrogenfluoride / dichloromethane / 20 h / 0 - 20 °C

2.1: sulfur trioxide pyridine complex / dichloromethane; dimethyl sulfoxide / 0.75 h / 0 - 20 °C

3.1: n-butyllithium / -78

3.2: 0.75 h / -78 °C

4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / chloroform / 0.17 h / 0 °C / pH 7

5.1: triethylamine / dichloromethane / 1 h / 0 - 20 °C

With n-butyllithium; sulfur trioxide pyridine complex; pyridine hydrogenfluoride; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; chloroform; -78; dimethyl sulfoxide;
DOI:10.1016/j.tetlet.2011.04.008