(3R,4R)-4-Amino-3-(1-carboxy-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid; compound with trifluoro-acetic acid

Base Information

• Chemical Name: (3R,4R)-4-Amino-3-(1-carboxy-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid; compound with trifluoro-acetic acid
• CAS No.: 97293-82-8
• Molecular Formula: C₂HF₃O₂*C₁₀H₁₁NO₅
• Molecular Weight: 339.225
• Mol file: 97293-82-8.mol

Synonyms:(3R,4R)-4-Amino-3-(1-carboxy-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid; compound with trifluoro-acetic acid

Chemical Property of (3R,4R)-4-Amino-3-(1-carboxy-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid; compound with trifluoro-acetic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R)-4-Amino-3-(1-carboxy-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid; compound with trifluoro-acetic acid

There total 6 articles about (3R,4R)-4-Amino-3-(1-carboxy-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid; compound with trifluoro-acetic 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: 68.0%

(3R,4R)-4-tert-Butoxycarbonylamino-3-(1-carboxy-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid + trifluoroacetic acid (76-05-1) → (3R,4R)-4-Amino-3-(1-carboxy-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid; compound with trifluoro-acetic acid (97293-82-8)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 0.25h;

DOI:10.1021/ja00303a038

Reference yield:

(3R,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-cyclohexa-1,5-dienecarboxylic acid methyl ester (97279-83-9) → (3R,4R)-4-Amino-3-(1-carboxy-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid; compound with trifluoro-acetic acid (97293-82-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 56 percent / Rh₂(OAc)4 / benzene / 70 °C

2: 94 percent / Et₃N / CH₂Cl₂ / Ambient temperature

3: CH₂Cl₂ / Ambient temperature

4: 47 percent / NaOH / tetrahydrofuran; H₂O

5: NaOH

6: 68 percent / tetrahydrofuran / 0.25 h / 0 °C

With dirhodium tetraacetate; sodium hydroxide; triethylamine; In tetrahydrofuran; dichloromethane; water; benzene;

DOI:10.1021/ja00303a038

Reference yield:

(3R,4R)-4-tert-Butoxycarbonylamino-3-(1-methoxycarbonyl-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid methyl ester (97279-87-3) → (3R,4R)-4-Amino-3-(1-carboxy-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid; compound with trifluoro-acetic acid (97293-82-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOH

2: 68 percent / tetrahydrofuran / 0.25 h / 0 °C

With sodium hydroxide; In tetrahydrofuran;

DOI:10.1021/ja00303a038

upstream raw materials:

trifluoroacetic acid

(3R,4R)-4-tert-Butoxycarbonylamino-3-hydroxy-cyclohexa-1,5-dienecarboxylic acid methyl ester

(3R,4R)-4-tert-Butoxycarbonylamino-3-(1-methoxycarbonyl-vinyloxy)-cyclohexa-1,5-dienecarboxylic acid methyl ester

2-((1S,6S)-6-tert-Butoxycarbonylamino-3-methoxycarbonyl-cyclohexa-2,4-dienyloxy)-malonic acid dimethyl ester

Downstream raw materials:

4-Amino-1-(2-carboxy-2-oxo-ethyl)-cyclohexa-2,5-dienecarboxylic acid; compound with trifluoro-acetic acid

4-amino-benzoic acid