(1S,3R,4R)-3-hydroxy-4-{(3E,5E,7E,9E,11Z)-11-[4-{(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]ethenyl}-5-oxofuran-2(5H)-ylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate

Base Information

• Chemical Name: (1S,3R,4R)-3-hydroxy-4-{(3E,5E,7E,9E,11Z)-11-[4-{(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]ethenyl}-5-oxofuran-2(5H)-ylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate
• CAS No.: 142633-11-2
• Molecular Formula: C₃₉H₅₀O₇
• Molecular Weight: 630.822
• Mol file: 142633-11-2.mol

Synonyms:

Chemical Property of (1S,3R,4R)-3-hydroxy-4-{(3E,5E,7E,9E,11Z)-11-[4-{(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]ethenyl}-5-oxofuran-2(5H)-ylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R,4R)-3-hydroxy-4-{(3E,5E,7E,9E,11Z)-11-[4-{(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]ethenyl}-5-oxofuran-2(5H)-ylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate

There total 13 articles about (1S,3R,4R)-3-hydroxy-4-{(3E,5E,7E,9E,11Z)-11-[4-{(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]ethenyl}-5-oxofuran-2(5H)-ylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate 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: 83.0%

11'Z-peridinin → peridinin (33281-81-1,58846-26-7,110270-07-0,128386-32-3,128386-43-6,142633-10-1,142633-11-2,142633-12-3,142633-15-6)

Guidance literature:

With triphenyl-arsane; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃; for 7h;

DOI:10.1002/chem.200600959

Reference yield: 72.0%

(1R,3S,6S)-6-[(E)-2-(tributylstannyl)ethenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol + (1S,3R)-4-[(3E,5Z,7E,9E,11Z)-11-(4-bromo-5-oxofuran-2(5H)-ylidene)-3,10-dimethylundeca-1,3,5,7,9-pentaenylidene]-3-hydroxy-3,5,5-trimethylcyclohexyl acetate → (1S,3R,4R)-3-hydroxy-4-{(3E,5E,7E,9E,11Z)-11-[4-{(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]ethenyl}-5-oxofuran-2(5H)-ylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate (33281-81-1,58846-26-7,110270-07-0,128386-32-3,128386-43-6,142633-10-1,142633-11-2,142633-12-3,142633-15-6)

Guidance literature:

With triphenyl-arsane; 2,6-di-tert-butyl-4-methyl-phenol; Tetrabutylammoniumsalz der Diphenylphosphinsaeure; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; at 55 ℃; for 31h;

DOI:10.1021/ol0478281

Reference yield: 69.0%

(1R,3S,6S)-6-[(E)-2-(tributylstannyl)ethenyl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol + C28H33BrO5 → peridinin (33281-81-1,58846-26-7,110270-07-0,128386-32-3,128386-43-6,142633-10-1,142633-11-2,142633-12-3,142633-15-6)

Guidance literature:

With triphenyl-arsane; Tetrabutylammoniumsalz der Diphenylphosphinsaeure; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; In tetrahydrofuran; at 55 ℃; for 19h;

DOI:10.1002/chem.200600959

upstream raw materials:

(5Z)-[(2'E)-2'-methyl-4'-oxo-1'-butenylidene]-3-[(1''E)-2''-(1'''S,2'''R,4'''S)-4'''-hydroxy-1''',2'''-epoxy-2''',6''',6'''-trimethylcyclohex-1'''-ylethen-1''-yl]-2(5H)-furanone

peridinin

(Z)-2-[(E)-2-((1S,4S,6R)-4-Hydroxy-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-vinyl]-4-oxo-but-2-enoic acid methyl ester

Downstream raw materials:

Acetic acid (1S,3R)-3-hydroxy-4-{(3E,5E,7E,9E)-11-[4-[(E)-2-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-vinyl]-5-oxo-5H-furan-(2Z)-ylidene]-3,10-dimethyl-undeca-1,3,5,7,9-pentaenylidene}-3,5,5-trimethyl-cyclohexyl ester

Acetic acid (1S,3R)-3-hydroxy-4-{(3E,5E,7E,9E)-11-[4-[(E)-2-((1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxa-bicyclo[4.1.0]hept-1-yl)-vinyl]-5-oxo-5H-furan-(2Z)-ylidene]-3,10-dimethyl-undeca-1,3,5,7,9-pentaenylidene}-3,5,5-trimethyl-cyclohexyl ester

(1S,3R,4R)-3-hydroxy-4-{(3E,5E,7E,9E,11Z)-11-[4-{(E)-2-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]hept-1-yl]ethenyl}-5-oxofuran-2(5H)-ylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate