R-(+)-benzyl 7-(3-hydroxy-5-oxo-1-cyclopentenyl)-5(Z)-heptenoate

Base Information

• Chemical Name: R-(+)-benzyl 7-(3-hydroxy-5-oxo-1-cyclopentenyl)-5(Z)-heptenoate
• CAS No.: 98497-13-3
• Molecular Formula: C₁₉H₂₂O₄
• Molecular Weight: 314.381
• Mol file: 98497-13-3.mol

Synonyms:R-(+)-benzyl 7-(3-hydroxy-5-oxo-1-cyclopentenyl)-5(Z)-heptenoate

Chemical Property of R-(+)-benzyl 7-(3-hydroxy-5-oxo-1-cyclopentenyl)-5(Z)-heptenoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of R-(+)-benzyl 7-(3-hydroxy-5-oxo-1-cyclopentenyl)-5(Z)-heptenoate

There total 3 articles about R-(+)-benzyl 7-(3-hydroxy-5-oxo-1-cyclopentenyl)-5(Z)-heptenoate 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: 60.0%

R,R-(-)-benzyl 7-(5-hydroxy-2-oxo-3-cyclopenten-1-yl)-5(Z)-heptenoate (98497-12-2) → R-(+)-benzyl 7-(3-hydroxy-5-oxo-1-cyclopentenyl)-5(Z)-heptenoate (98497-13-3)

Guidance literature:

With aluminum oxide; In diethyl ether; water; Ambient temperature;

DOI:10.1016/S0040-4020(01)96437-3

Reference yield:

(-)-benzyl <7-(5α-hydroxy-2,3-α-epoxycyclopent-α-yl)>-5(Z)-heptenoate (98497-08-6) → R-(+)-benzyl 7-(3-hydroxy-5-oxo-1-cyclopentenyl)-5(Z)-heptenoate (98497-13-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / pyridinium dichromate (PDC) / dimethylformamide / Ambient temperature

2: 96 percent / Et₃N / diethyl ether; CH₂Cl₂

3: 60 percent / alumina / diethyl ether; H₂O / Ambient temperature

With aluminum oxide; dipyridinium dichromate; triethylamine; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)96437-3

Reference yield:

(-)-benzyl <7-(2,3-α-epoxy-5-oxo-cyclopent-α-yl)>-5(Z)-heptenoate (98497-10-0) → R-(+)-benzyl 7-(3-hydroxy-5-oxo-1-cyclopentenyl)-5(Z)-heptenoate (98497-13-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Et₃N / diethyl ether; CH₂Cl₂

2: 60 percent / alumina / diethyl ether; H₂O / Ambient temperature

With aluminum oxide; triethylamine; In diethyl ether; dichloromethane; water;

DOI:10.1016/S0040-4020(01)96437-3

upstream raw materials:

R,R-(-)-benzyl 7-(5-hydroxy-2-oxo-3-cyclopenten-1-yl)-5(Z)-heptenoate

(-)-benzyl <7-(5α-hydroxy-2,3-α-epoxycyclopent-α-yl)>-5(Z)-heptenoate

(-)-benzyl <7-(2,3-α-epoxy-5-oxo-cyclopent-α-yl)>-5(Z)-heptenoate

Downstream raw materials:

(Z)-7-[(R)-3-(tert-Butyl-dimethyl-silanyloxy)-5-oxo-cyclopent-1-enyl]-hept-5-enoic acid benzyl ester