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

Base Information

• Chemical Name: (1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxohept-1-enyl)cyclopentane
• CAS No.: 358395-68-3
• Molecular Formula: C₃₂H₃₆O₉
• Molecular Weight: 564.632
• Mol file: 358395-68-3.mol

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

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

There total 13 articles about (1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxohept-1-enyl)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: 89.0%

diethyl [6-(methoxycarbonyl)-2-oxohexyl]phosphonate (329980-67-8) + (1R,2R,3S,4S)-1,4-di(benzoyloxy)-2-formyl-3-(2-methoxycarbonylethyl)cyclopentane (358395-65-0) → Benzoic acid (1S,2S)-2-(2-methoxycarbonyl-ethyl)-3-((E)-7-methoxycarbonyl-3-oxo-hept-1-enyl)-cyclopent-3-enyl ester + (1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxohept-1-enyl)cyclopentane (358395-68-3)

Guidance literature:

With sodium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)00754-7

Reference yield:

Dimethyl <6-(methoxycarbonyl)-2-oxohexyl>phosphonate (58648-51-4) + (1R,2R,3S,4S)-1,4-di(benzoyloxy)-2-formyl-3-(2-methoxycarbonylethyl)cyclopentane (358395-65-0) → (1R,2R,3S,4S)-1,4-di(benzoyloxy)-3-(2-methoxycarbonylethyl)-2-(7-methoxycarbonyl-3-oxohept-1-enyl)cyclopentane (358395-68-3)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.166667h;

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-oxohept-1-enyl)cyclopentane (358395-68-3)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium hydride; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; water; 1: Dess-Martin oxidation;

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

upstream raw materials:

diethyl [6-(methoxycarbonyl)-2-oxohexyl]phosphonate

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

Dimethyl <6-(methoxycarbonyl)-2-oxohexyl>phosphonate

benzoyl chloride

Downstream raw materials:

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

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