4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanoic acid

Base Information

• Chemical Name: 4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanoic acid
• CAS No.: 1061330-20-8
• Molecular Formula: C₂₈H₃₈O₆
• Molecular Weight: 470.606
• Mol file: 1061330-20-8.mol

Synonyms:4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanoic acid

Chemical Property of 4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanoic acid

There total 18 articles about 4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanoic acid 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%

4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanal (1061330-18-4) → 4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanoic acid (1061330-20-8)

Guidance literature:

With sodium chlorite; sodium dihydrogenphosphate; In water; tert-butyl alcohol; at 20 ℃; for 1h;

DOI:10.1021/ol500654g

Reference yield:

(3R,4R,E)-2-(((2R,3R)-3-(4-hydroxybutyl)oxiran-2-yl)methylene)-4-((4-methoxybenzyl)oxy)-3-((Z)-oct-2-en-1-yl)cyclopentanone → 4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanoic acid (1061330-20-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 21 °C / Inert atmosphere

2: sodium chlorite; sodium dihydrogen phosphate monohydrate / tert-butyl alcohol; water / 1 h / 21 °C / Inert atmosphere

With sodium chlorite; sodium dihydrogen phosphate monohydrate; sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jm400959q

Reference yield:

(3R,4R,E)-2-(((2R,3R)-3-(4-((tert-butyldimethylsilyl)oxy)butyl)oxiran-2-yl)methylene)-4-((4-methoxybenzyl)oxy)-3-((Z)-oct-2-en-1-yl)cyclopentanone (1061330-17-3) → 4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanoic acid (1061330-20-8)

Guidance literature:

Multi-step reaction with 3 steps

1: formic acid / tetrahydrofuran; water / 1 h / 21 °C / Inert atmosphere

2: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 1 h / 0 - 21 °C / Inert atmosphere

3: sodium chlorite; sodium dihydrogen phosphate monohydrate / tert-butyl alcohol; water / 1 h / 21 °C / Inert atmosphere

With sodium chlorite; formic acid; sodium dihydrogen phosphate monohydrate; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jm400959q

upstream raw materials:

4-[(2R,3R)-3-((E)-((2R,3R)-3-(4-methoxyphenylmethoxy)-2-((Z)-oct-2-enyl)-5-oxo-cyclopentylidene)methyl)oxiran-2-yl]butanal

(R)-4-(4-methoxyphenylmethoxy)cyclopent-2-enone

(R)-2-bromo-4-(4-methoxyphenylmethoxy)cyclopent-2-enone

2-[(1S,5R)-2-bromo-3-[(1,1-dimethylethyl)dimethylsilyloxy]-5-(4-methoxyphenylmethoxy)cyclopent-2-enyl]acetaldehyde