2-[(1S,2R)-2-(6-Methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

Base Information

• Chemical Name: 2-[(1S,2R)-2-(6-Methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester
• CAS No.: 207991-40-0
• Molecular Formula: C₃₁H₃₈O₇
• Molecular Weight: 522.639
• Mol file: 207991-40-0.mol

Synonyms:2-[(1S,2R)-2-(6-Methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

Chemical Property of 2-[(1S,2R)-2-(6-Methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(1S,2R)-2-(6-Methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

There total 3 articles about 2-[(1S,2R)-2-(6-Methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester 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: 46.0%

2-{(1S,2S)-2-[1-(Imidazole-1-carbothioyloxy)-6-methoxycarbonyl-hexyl]-3-oxo-cyclopentyl}-2-methyl-malonic acid dibenzyl ester (207991-54-6) → 2-[(1S,2R)-2-(6-Methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester (207991-40-0)

Guidance literature:

With di-tert-butyl peroxide; tri-n-butyl-tin hydride; at 50 ℃;

DOI:10.1021/jo9723319

Reference yield:

2-[(1S,2S)-2-(1-Hydroxy-6-methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester → 2-[(1S,2R)-2-(6-Methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester (207991-40-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 53 percent / DMAP / acetonitrile

2: 46 percent / Bu₃SnH, (t-BuO)2 / 50 °C

With dmap; di-tert-butyl peroxide; tri-n-butyl-tin hydride; In acetonitrile;

DOI:10.1021/jo9723319

Reference yield:

2-{(S)-2-[6-Methoxycarbonyl-hex-(E)-ylidene]-3-oxo-cyclopentyl}-2-methyl-malonic acid dibenzyl ester (207991-39-7) → 2-[(1S,2R)-2-(6-Methoxycarbonyl-hexyl)-3-oxo-cyclopentyl]-2-methyl-malonic acid dibenzyl ester (207991-40-0)

Guidance literature:

With triethylsilane; Wilkinson's catalyst; hydrogen fluoride; Yield given. Multistep reaction; 1.) 80 deg C, 15 min, 2.) CH₃CN, H₂O, room temperature, 6 h;

DOI:10.1021/jo9723319

upstream raw materials:

2-{(S)-2-[6-Methoxycarbonyl-hex-(E)-ylidene]-3-oxo-cyclopentyl}-2-methyl-malonic acid dibenzyl ester

2-{(1S,2S)-2-[1-(Imidazole-1-carbothioyloxy)-6-methoxycarbonyl-hexyl]-3-oxo-cyclopentyl}-2-methyl-malonic acid dibenzyl ester

Downstream raw materials:

2-[(1S,2R,3S)-3-(tert-Butyl-dimethyl-silanyloxy)-2-(6-methoxycarbonyl-hexyl)-cyclopentyl]-2-methyl-malonic acid dibenzyl ester

2-[(1S,2R,3S)-3-Hydroxy-2-(6-methoxycarbonyl-hexyl)-cyclopentyl]-2-methyl-malonic acid dibenzyl ester