beta-citrylglutamic acid

Base Information

• Chemical Name: beta-citrylglutamic acid
• CAS No.: 69281-09-0
• Molecular Formula: C₁₁H₁₅NO₁₀
• Molecular Weight: 321.241
• Mol file: 69281-09-0.mol

Synonyms:

Chemical Property of beta-citrylglutamic acid

Chemical Property:

• Vapor Pressure: 1.2E-24mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of beta-citrylglutamic acid

There total 5 articles about beta-citrylglutamic 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: 42.0%

2-{(1S)-[1,3-bis(benzylcarboxy)prop-1-yl]carbamoyl}-1,3-bis(benzylcarboxy)-2-carboxy-2-hydroxypropan-2-amide → β-citryl-L-glutamic acid (69281-09-0)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; for 3h; under 798.054 Torr;

DOI:10.1111/febs.13761

Reference yield:

1,5-dimethyl citrate (53798-96-2) → β-citryl-L-glutamic acid (69281-09-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sulfuric acid / 18 h / -78 - 20 °C

2.1: water; sodium hydroxide / methanol / 6 h / 0 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h / Reflux

4.1: trifluoroacetic acid / 0.42 h

5.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h

5.2: 2.5 h

6.1: palladium on activated charcoal; hydrogen / methanol / 3 h / 798.05 Torr

With sulfuric acid; palladium on activated charcoal; water; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1111/febs.13761

Reference yield:

2-tert-butyl 1,3-dimethyl 2-hydroxypropane-1,2,3-tricarboxylate (114340-51-1) → β-citryl-L-glutamic acid (69281-09-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: water; sodium hydroxide / methanol / 6 h / 0 °C

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / acetonitrile / 2 h / Reflux

3.1: trifluoroacetic acid / 0.42 h

4.1: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.25 h

4.2: 2.5 h

5.1: palladium on activated charcoal; hydrogen / methanol / 3 h / 798.05 Torr

With palladium on activated charcoal; water; hydrogen; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1111/febs.13761

upstream raw materials:

1,5-dimethyl citrate

2-tert-butyl 1,3-dimethyl 2-hydroxypropane-1,2,3-tricarboxylate

3-(tert-butoxycarbonyl)-3-hydroxypentanedioic acid

Refernces