(5S,4'S,5'S,8'EZ,10'E,12'E)-N-benzoyl-3-(8,12-dimethyl-4,5-isopropylidenedioxy-1-oxotetradeca-8,10,12-trienyl)-5-(2-methylpropyl)-3-phenylselenopyrrolidin-2-one

Base Information

Chemical Name:(5S,4'S,5'S,8'EZ,10'E,12'E)-N-benzoyl-3-(8,12-dimethyl-4,5-isopropylidenedioxy-1-oxotetradeca-8,10,12-trienyl)-5-(2-methylpropyl)-3-phenylselenopyrrolidin-2-one
CAS No.:124575-47-9
Molecular Formula:C₄₀H₅₁NO₅Se
Molecular Weight:704.809
Hs Code.:

(5S,4'S,5'S,8'EZ,10'E,12'E)-N-benzoyl-3-(8,12-dimethyl-4,5-isopropylidenedioxy-1-oxotetradeca-8,10,12-trienyl)-5-(2-methylpropyl)-3-phenylselenopyrrolidin-2-one

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Chemical Property of (5S,4'S,5'S,8'EZ,10'E,12'E)-N-benzoyl-3-(8,12-dimethyl-4,5-isopropylidenedioxy-1-oxotetradeca-8,10,12-trienyl)-5-(2-methylpropyl)-3-phenylselenopyrrolidin-2-one

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Technology Process of (5S,4'S,5'S,8'EZ,10'E,12'E)-N-benzoyl-3-(8,12-dimethyl-4,5-isopropylidenedioxy-1-oxotetradeca-8,10,12-trienyl)-5-(2-methylpropyl)-3-phenylselenopyrrolidin-2-one

There total 17 articles about (5S,4'S,5'S,8'EZ,10'E,12'E)-N-benzoyl-3-(8,12-dimethyl-4,5-isopropylidenedioxy-1-oxotetradeca-8,10,12-trienyl)-5-(2-methylpropyl)-3-phenylselenopyrrolidin-2-one 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: 80.0%

: 5707-04-0
Phenylselenyl chloride

: 124575-46-8,124602-07-9,124602-08-0,124602-09-1
(S)-1-Benzoyl-3-{3-[(4S,5S)-5-((3E,5E,7E)-3,7-dimethyl-nona-3,5,7-trienyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-propionyl}-5-isobutyl-pyrrolidin-2-one

: 124575-47-9,124602-10-4,124602-11-5,124602-12-6
(5S,4'S,5'S,8'EZ,10'E,12'E)-N-benzoyl-3-(8,12-dimethyl-4,5-isopropylidenedioxy-1-oxotetradeca-8,10,12-trienyl)-5-(2-methylpropyl)-3-phenylselenopyrrolidin-2-one

Guidance literature:: With lithium hexamethyldisilazane; In tetrahydrofuran; hexane; at -78 ℃; for 4h;
DOI:10.1016/S0040-4020(01)83439-6

Reference yield:

: 77332-99-1
(+)-(4R-trans)-5-<(benzoyloxy)methyl>-2,2-dimethyl-1,3-dioxolane-4-carboxaldehyde

: 124575-47-9,124602-10-4,124602-11-5,124602-12-6
(5S,4'S,5'S,8'EZ,10'E,12'E)-N-benzoyl-3-(8,12-dimethyl-4,5-isopropylidenedioxy-1-oxotetradeca-8,10,12-trienyl)-5-(2-methylpropyl)-3-phenylselenopyrrolidin-2-one

Guidance literature:: Multi-step reaction with 11 steps

1: 60 percent / NaH / 1,2-dimethoxy-ethane / 1.83 h / 0 °C

2: 79 percent / H₂ / Pd/C / ethanol / 2.5 h / Ambient temperature

3: 91 percent / Na / ethanol / 0.25 h

4: DMSO, oxalyl chloride, Et₃N / CH₂Cl₂ / 0.75 h / -78 °C

5: 72 percent / benzene / 16 h / Heating

6: 88 percent / H₂ / Pd/C / ethyl acetate

8: 97 percent / NaOH / ethanol; H₂O / 1.5 h / Ambient temperature

9: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature

10: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C

11: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C

With sodium hydroxide; oxalyl dichloride; hydrogen; sodium; sodium hydride; dimethyl sulfoxide; triethylamine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; water; ethyl acetate; benzene;
DOI:10.1016/S0040-4020(01)83439-6

Reference yield:

: 124575-40-2
ethyl 3-((4S,5R)-5-formyl-2,2-dimethyl-1,3-dioxolan-4-yl)propanoate

: 124575-47-9,124602-10-4,124602-11-5,124602-12-6
(5S,4'S,5'S,8'EZ,10'E,12'E)-N-benzoyl-3-(8,12-dimethyl-4,5-isopropylidenedioxy-1-oxotetradeca-8,10,12-trienyl)-5-(2-methylpropyl)-3-phenylselenopyrrolidin-2-one

Guidance literature:: Multi-step reaction with 7 steps

1: 72 percent / benzene / 16 h / Heating

2: 88 percent / H₂ / Pd/C / ethyl acetate

4: 97 percent / NaOH / ethanol; H₂O / 1.5 h / Ambient temperature

5: 92 percent / benzene; tetrahydrofuran / 18 h / Ambient temperature

6: lithium hexamethyldisilazide / tetrahydrofuran; hexane / 8.5 h / -78 °C

7: 80 percent / lithium hexamethyldisilazide / tetrahydrofuran; hexane / 4 h / -78 °C

With sodium hydroxide; hydrogen; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; water; ethyl acetate; benzene;
DOI:10.1016/S0040-4020(01)83439-6