(1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxoheptyl)cyclopentane

Base Information

• Chemical Name: (1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxoheptyl)cyclopentane
• CAS No.: 552833-10-0
• Molecular Formula: C₃₂H₃₈O₉
• Molecular Weight: 566.648
• Mol file: 552833-10-0.mol

Synonyms:(1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxoheptyl)cyclopentane

Chemical Property of (1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxoheptyl)cyclopentane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxoheptyl)cyclopentane

There total 11 articles about (1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxoheptyl)cyclopentane 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: 100.0%

(1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxohept-1-enyl)cyclopentane (358395-68-3) → (1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxoheptyl)cyclopentane (552833-10-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 4h; atmospheric pressure;

DOI:10.1016/S0040-4020(03)00258-8

Reference yield:

(1R,2S,3S,4S)-1,4-di(benzoyloxy)-2-hydroxymethyl-3-(2-methoxycarbonylethyl)cyclopentane (358395-64-9) → (1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxoheptyl)cyclopentane (552833-10-0)

Guidance literature:

Multi-step reaction with 3 steps

1: Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.5 h / 20 °C

2: 258 mg / NaH / tetrahydrofuran / 0.17 h / 20 °C

3: 100 percent / H₂ / 10 percent Pd/C / ethanol / 4 h / atmospheric pressure

With hydrogen; sodium hydride; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; water; 1: Dess-Martin oxidation;

DOI:10.1016/S0040-4020(03)00258-8

Reference yield:

(1R,2S,3S,4S)-1,4-bis-O-(benzoyl)-2-(tert-butyldiphenylsilyloxymethyl)-3-(methoxycarbonylethyl)cyclopentane-1,4-diol (358395-57-0) → (1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxoheptyl)cyclopentane (552833-10-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 68 percent / HCl / diethyl ether; methanol / 20 h / 20 °C

2: Dess-Martin periodinane / CH₂Cl₂; H₂O / 0.5 h / 20 °C

3: 258 mg / NaH / tetrahydrofuran / 0.17 h / 20 °C

4: 100 percent / H₂ / 10 percent Pd/C / ethanol / 4 h / atmospheric pressure

With hydrogenchloride; hydrogen; sodium hydride; Dess-Martin periodane; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water; 2: Dess-Martin oxidation;

DOI:10.1016/S0040-4020(03)00258-8

upstream raw materials:

(1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxohept-1-enyl)cyclopentane

benzoyl chloride

(1R,2S,3S,4S)-1,4-di(benzoyloxy)-2-hydroxymethyl-3-(2-methoxycarbonylethyl)cyclopentane

(2S,4R,5R)-6-(tert-butyldiphenylsilyloxy)-1,1-diethylthio-5-iodohexane-2,4-diol

Downstream raw materials:

8-[(1R,2S,3S,5R)-2-(2-Carboxy-ethyl)-3,5-dihydroxy-cyclopentyl]-6-oxo-octanoic acid