(9Z,12Z)-(15S,16S)-15-Bromo-16-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-octadeca-9,12-dienoic acid methyl ester

Base Information

Chemical Name:(9Z,12Z)-(15S,16S)-15-Bromo-16-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-octadeca-9,12-dienoic acid methyl ester
CAS No.:271780-37-1
Molecular Formula:C₂₉H₄₀BrF₃O₅
Molecular Weight:605.533
Hs Code.:

Synonyms:(9Z,12Z)-(15S,16S)-15-Bromo-16-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-octadeca-9,12-dienoic acid methyl ester

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Chemical Property of (9Z,12Z)-(15S,16S)-15-Bromo-16-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-octadeca-9,12-dienoic acid methyl ester

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Technology Process of (9Z,12Z)-(15S,16S)-15-Bromo-16-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-octadeca-9,12-dienoic acid methyl ester

There total 3 articles about (9Z,12Z)-(15S,16S)-15-Bromo-16-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-octadeca-9,12-dienoic acid methyl ester 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%

: 17257-71-5,20445-31-2,56135-03-6,81655-41-6
(S)-Mosher acid

: 271780-34-8
(9Z,12Z)-(15S,16S)-15-Bromo-16-hydroxy-octadeca-9,12-dienoic acid methyl ester

: 271780-37-1
(9Z,12Z)-(15S,16S)-15-Bromo-16-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-octadeca-9,12-dienoic acid methyl ester

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 20 ℃; for 46h;
DOI:10.3987/COM-99-S147

Reference yield:

: 301-00-8
methyl linolenate

: 271780-37-1
(9Z,12Z)-(15S,16S)-15-Bromo-16-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-octadeca-9,12-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 35 percent / NBS; water / 1,2-dimethoxy-ethane

2: 49 percent / lipase PS; 4 Angstroem molecular sieves; 1,4,8,11-tetrathiacyclotetradecane / hexane / 20 h / 20 °C

3: 85 percent / DCC; DMAP / CH₂Cl₂ / 46 h / 20 °C

With dmap; 1,4,8,11-tetrathiacyclotetradecane; N-Bromosuccinimide; Lipase PS; 4 A molecular sieve; water; dicyclohexyl-carbodiimide; In 1,2-dimethoxyethane; hexane; dichloromethane; 1: Oxidation / 2: Acetylation / 3: Esterification;
DOI:10.3987/COM-99-S147

Reference yield:

: 271780-31-5
15-bromo-16-hydroxy-α-linolenic acid methyl ester

: 271780-37-1
(9Z,12Z)-(15S,16S)-15-Bromo-16-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-octadeca-9,12-dienoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 49 percent / lipase PS; 4 Angstroem molecular sieves; 1,4,8,11-tetrathiacyclotetradecane / hexane / 20 h / 20 °C

2: 85 percent / DCC; DMAP / CH₂Cl₂ / 46 h / 20 °C

With dmap; 1,4,8,11-tetrathiacyclotetradecane; Lipase PS; 4 A molecular sieve; dicyclohexyl-carbodiimide; In hexane; dichloromethane; 1: Acetylation / 2: Esterification;
DOI:10.3987/COM-99-S147