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

Base Information

• Chemical Name: (S)-5-hydroxy-3-phenylpentyl acetate
• CAS No.: 153363-11-2
• Molecular Formula: C₁₃H₁₈O₃
• Molecular Weight: 222.284
• Mol file: 153363-11-2.mol

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

Chemical Property of (S)-5-hydroxy-3-phenylpentyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-5-hydroxy-3-phenylpentyl acetate

There total 12 articles about (S)-5-hydroxy-3-phenylpentyl 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: 52.0%

vinyl acetate (108-05-4,9003-20-7) + 3-phenylpentane-1,5-diol (829-27-6) → (S)-5-hydroxy-3-phenylpentyl acetate (153363-11-2)

Guidance literature:

With AK lipase; at 4 ℃; for 25h;

DOI:10.1021/jo2007972

Reference yield:

3-phenylpentane-1,5-diyl diacetate (1263798-11-3) → (R)-5-hydroxy-3-phenylpentyl acetate (1263798-71-5) + (S)-5-hydroxy-3-phenylpentyl acetate (153363-11-2)

Guidance literature:

With AK lipase; water; In acetonitrile; at 30 ℃; for 14h; pH=7; optical yield given as %ee; enantioselective reaction; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1021/jo101962v

Reference yield:

diethyl 3-phenylpentanedioate (55951-74-1) → (S)-5-hydroxy-3-phenylpentyl acetate (153363-11-2)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / diethyl ether / 14 h / 20 °C / Inert atmosphere

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

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

With dmap; lithium aluminium tetrahydride; AK lipase; water; triethylamine; In diethyl ether; dichloromethane; acetonitrile;

DOI:10.1021/jo101962v

upstream raw materials:

vinyl acetate

3-phenylpentane-1,5-diol

3-phenylpentane-1,5-diyl diacetate

3-phenylglutaric acid

Downstream raw materials:

5-(acetyloxy)-3-phenylpentanoic acid

5-(acetyloxy)-3-phenylpentyl 3,3,3-trifluoro-2-methoxy-2-phenylpropanoate

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

(S)-5-amino-3-phenylpentan-1-ol

Refernces

• 1、 Rios-Lombardia, Nicolas,Busto, Eduardo,Gotor-Fernandez, Vicente,Gotor, Vicente. "Chemoenzymatic asymmetric synthesis of optically active pentane-1,5-diamine fragments by means of lipase-catalyzed desymmetrization transformations". scheme or table. p. 5709 - 5718. Retrieved 2011/09/16.