Benzenepropanoic acid, -ba--[2-(acetyloxy)ethyl]-, (-ba-R)- (9CI)

Base Information

• Chemical Name: Benzenepropanoic acid, -ba--[2-(acetyloxy)ethyl]-, (-ba-R)- (9CI)
• CAS No.: 536972-25-5
• Molecular Formula: C13H16O4
• Molecular Weight: 236.26
• Mol file: 536972-25-5.mol

Synonyms:Benzenepropanoicacid,-bta--[2-(acetyloxy)ethyl]-,(-bta-R)-(9CI);Benzenepropanoic acid, -ba--[2-(acetyloxy)ethyl]-, (-ba-R)- (9CI)

Chemical Property of Benzenepropanoic acid, -ba--[2-(acetyloxy)ethyl]-, (-ba-R)- (9CI)

Chemical Property:

• PSA: 63.60000
• LogP: 2.19810

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzenepropanoic acid, -ba--[2-(acetyloxy)ethyl]-, (-ba-R)- (9CI)

There total 5 articles about Benzenepropanoic acid, -ba--[2-(acetyloxy)ethyl]-, (-ba-R)- (9CI) 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: 84.0%

(S)-5-hydroxy-3-phenylpentyl acetate (153363-11-2) → 5-(acetyloxy)-3-phenylpentanoic acid (536972-25-5)

Guidance literature:

With Jones reagent; In acetone; at 20 ℃; for 1h;

DOI:10.1021/jo101962v

Reference yield: 58.0%

Acetic acid (S)-3-phenyl-hex-5-enyl ester (85000-04-0) → 5-(acetyloxy)-3-phenylpentanoic acid (536972-25-5)

Guidance literature:

With ruthenium(IV) oxide; sodium periodate; In dichloromethane; acetonitrile; at 20 ℃; for 4h;

DOI:10.1021/jm0204587

Reference yield:

3-phenylpentane-1,5-diol (829-27-6) → 5-(acetyloxy)-3-phenylpentanoic acid (536972-25-5)

Guidance literature:

Multi-step reaction with 3 steps

1: dmap; triethylamine / dichloromethane / 4 h / 20 °C / Inert atmosphere

2: AK lipase; water / acetonitrile / 40 h / 30 °C / pH 7 / aq. phosphate buffer; Enzymatic reaction

3: Jones reagent / acetone / 1 h / 20 °C

With dmap; Jones reagent; AK lipase; water; triethylamine; In dichloromethane; acetone; acetonitrile;

DOI:10.1021/jo101962v

upstream raw materials:

Acetic acid (S)-3-phenyl-hex-5-enyl ester

3-phenylpentane-1,5-diyl diacetate

(S)-5-hydroxy-3-phenylpentyl acetate

3-phenylpentane-1,5-diol

Downstream raw materials:

(4S,5S)-4-Benzyl-5-[(S)-2-benzyl-3-oxo-4-((R)-1-oxo-1,2,3,4-tetrahydro-isoquinolin-4-yl)-2,3-dihydro-1H-pyrrol-2-ylmethyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Acetic acid (S)-4-isocyanato-3-phenyl-butyl ester

Acetic acid (R)-4-azidocarbonyl-3-phenyl-butyl ester

Refernces

• 1、 Smith III, Amos B.,Cantin, Louis-David,Pasternak, Alexander,Guise-Zawacki, Lisa,Yao, Wenquin,Charnley, Adam K.,Barbosa, Joseph,Sprengeler, Paul A.,Hirschmann, Ralph,Munshi, Sanjeev,Olsen, David B.,Schleif, William A.,Kuo, Lawrence C.. "Design, synthesis, and biological evaluation of monopyrrolinone-based HIV-1 protease inhibitors". . p. 1831 - 1844. Retrieved 2007/10/03.