(R,R,E,E)-3-(n-benzyloxycarbonylamino)-4-[N(3')-(2'',4''-hexadienoyl)-2',2'-dimethyl-1',3'-oxazolidin-5'-yl]butanoic acid

Base Information

• Chemical Name: (R,R,E,E)-3-(n-benzyloxycarbonylamino)-4-[N(3')-(2'',4''-hexadienoyl)-2',2'-dimethyl-1',3'-oxazolidin-5'-yl]butanoic acid
• CAS No.: 1262515-97-8
• Molecular Formula: C₂₃H₃₀N₂O₆
• Molecular Weight: 430.501
• Mol file: 1262515-97-8.mol

Synonyms:(R,R,E,E)-3-(n-benzyloxycarbonylamino)-4-[N(3')-(2'',4''-hexadienoyl)-2',2'-dimethyl-1',3'-oxazolidin-5'-yl]butanoic acid

Chemical Property of (R,R,E,E)-3-(n-benzyloxycarbonylamino)-4-[N(3')-(2'',4''-hexadienoyl)-2',2'-dimethyl-1',3'-oxazolidin-5'-yl]butanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,R,E,E)-3-(n-benzyloxycarbonylamino)-4-[N(3')-(2'',4''-hexadienoyl)-2',2'-dimethyl-1',3'-oxazolidin-5'-yl]butanoic acid

There total 8 articles about (R,R,E,E)-3-(n-benzyloxycarbonylamino)-4-[N(3')-(2'',4''-hexadienoyl)-2',2'-dimethyl-1',3'-oxazolidin-5'-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: 88.0%

methyl (R,R,E,E)-3-(N-benzyloxycarbonylamino)-4-[2',2'-dimethyl-N(3')-(2,4-hexadienoyl)-1',3'-oxazolidin-5'-yl]butanoate (1262515-96-7) → (R,R,E,E)-3-(n-benzyloxycarbonylamino)-4-[N(3')-(2'',4''-hexadienoyl)-2',2'-dimethyl-1',3'-oxazolidin-5'-yl]butanoic acid (1262515-97-8)

Guidance literature:

methyl (R,R,E,E)-3-(N-benzyloxycarbonylamino)-4-[2',2'-dimethyl-N(3')-(2,4-hexadienoyl)-1',3'-oxazolidin-5'-yl]butanoate; With water; sodium hydroxide; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 4h;

With potassium hydrogensulfate; In water; pH=4;

DOI:10.1016/j.tet.2010.10.067

Reference yield:

C15H22N2O5*ClH (1262515-95-6) → (R,R,E,E)-3-(n-benzyloxycarbonylamino)-4-[N(3')-(2'',4''-hexadienoyl)-2',2'-dimethyl-1',3'-oxazolidin-5'-yl]butanoic acid (1262515-97-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / Inert atmosphere

1.2: 1 h / 0 °C / Inert atmosphere

2.1: toluene-4-sulfonic acid / acetone / 26 h / 20 °C / Inert atmosphere

3.1: water; sodium hydroxide / tetrahydrofuran; methanol / 4 h / 0 - 20 °C

3.2: pH 4

With water; toluene-4-sulfonic acid; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; acetone;

DOI:10.1016/j.tet.2010.10.067

Reference yield:

3'-pentyl (R,R)-3-amino-4-[2',2-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]butanoate (1262515-93-4) → (R,R,E,E)-3-(n-benzyloxycarbonylamino)-4-[N(3')-(2'',4''-hexadienoyl)-2',2'-dimethyl-1',3'-oxazolidin-5'-yl]butanoic acid (1262515-97-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium hydrogencarbonate; sodium chloride / dichloromethane; chloroform; water / 0.75 h / 20 °C

2.1: hydrogenchloride / 0.52 h / 0 °C

3.1: triethylamine / dichloromethane / Inert atmosphere

3.2: 1 h / 0 °C / Inert atmosphere

4.1: toluene-4-sulfonic acid / acetone / 26 h / 20 °C / Inert atmosphere

5.1: water; sodium hydroxide / tetrahydrofuran; methanol / 4 h / 0 - 20 °C

5.2: pH 4

With hydrogenchloride; water; sodium hydrogencarbonate; toluene-4-sulfonic acid; triethylamine; sodium chloride; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; chloroform; water; acetone;

DOI:10.1016/j.tet.2010.10.067

upstream raw materials:

3'-pentyl (R,R)-3-amino-4-[2',2-dimethyl-N(3')-tert-butoxycarbonyl-1',3'-oxazolidin-5'-yl]butanoate

3'-pentyl (R,R)-3-(N-benzyloxycarbonylamino)-4-[N(3')-tert-butoxycarbonyl-2',2'-dimethyl-1',3-oxazolidin-5'-yl]butanoate

C₁₅H₂₂N₂O₅*ClH

methyl (R,R,E,E)-3-(N-benzyloxycarbonylamino)-5-hydroxy-6-[N-(2',4'-hexadienoyl)amino]hexanoate

Downstream raw materials:

2'-amidinoethyl (R,R,E,E)-3-amino-5-hydroxy-6-[N-(2'',4''-hexadienoyl)amino]butanamide