(5R,7S,8E)-5-Hydroxy-7-acetoxy-9-phenyl-2,8-nonadienoic acid lactone

Base Information

• Chemical Name: (5R,7S,8E)-5-Hydroxy-7-acetoxy-9-phenyl-2,8-nonadienoic acid lactone
• CAS No.: 34427-30-0
• Molecular Formula: C₁₇H₁₈O₄
• Molecular Weight: 286.328
• Mol file: 34427-30-0.mol

Synonyms:

Chemical Property of (5R,7S,8E)-5-Hydroxy-7-acetoxy-9-phenyl-2,8-nonadienoic acid lactone

Chemical Property:

• Melting Point: 125-126 °C
• Boiling Point: 480.7±38.0 °C(Predicted)
• PSA: 0.00000
• Density: 1.158±0.06 g/cm3(Predicted)
• LogP: 0.00000

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,7S,8E)-5-Hydroxy-7-acetoxy-9-phenyl-2,8-nonadienoic acid lactone

There total 42 articles about (5R,7S,8E)-5-Hydroxy-7-acetoxy-9-phenyl-2,8-nonadienoic acid lactone 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: 90.0%

(R)-6-((S,E)-2-hydroxy-4-phenylbut-3-en-1-yl)-5,6-dihydro-2H-pyran-2-one (91327-34-3) + acetic anhydride (108-24-7) → (S,E)-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-4-phenylbut-3-en-2-yl acetate (67144-65-4,67144-66-5,91382-78-4,94534-93-7,34427-30-0)

Guidance literature:

(R)-6-((S,E)-2-hydroxy-4-phenylbut-3-en-1-yl)-5,6-dihydro-2H-pyran-2-one; With dmap; triethylamine; In dichloromethane; at 0 ℃; for 0.0833333h;

acetic anhydride; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;

DOI:10.1002/anie.201709844

Reference yield: 62.0%

(S)-6-((S,E)-2-hydroxy-4-phenylbut-3-enyl)-5,6-dihydro-2H-pyran-2-one (91327-33-2) + acetic anhydride (108-24-7) → (S,E)-1-((S)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-4-phenylbut-3-en-2-yl acetate (34427-30-0,67144-65-4,67144-66-5,94534-93-7,91382-78-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1016/j.tetlet.2012.02.073

Reference yield: 58.0%

(1R,3S,4E)-3-acetoxy-1-allyl-5-phenyl-4-penteny acrylate (1190769-83-5) → (S,E)-1-((R)-6-oxo-3,6-dihydro-2H-pyran-2-yl)-4-phenylbut-3-en-2-yl acetate (67144-65-4,67144-66-5,91382-78-4,94534-93-7,34427-30-0)

Guidance literature:

With Grubbs catalyst first generation; In dichloromethane; for 8h; Inert atmosphere; Reflux;

DOI:10.3762/bjoc.5.14

upstream raw materials:

acetic anhydride

<6RS(2S,3E)>-(+)-5,6-Dihydro-6-(2-hydroxy-4-phenyl-3-butenyl)-2H-pyran-2-on

<6RS<2S(2RS),3E>>-5,6-Dihydro-6-<4-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)-3-butenyl>-2H-pyran-2-on

<6RS<2S(2RS),3E>>-5,6-Dihydro-6-<4-phenyl-2-(tetrahydro-2H-pyran-2-yloxy)-3-butenyl>-2H-pyran-2,4(3H)-dion