N-Fmoc-D-Glutamic acid 1-methyl ester

Base Information

• Chemical Name: N-Fmoc-D-Glutamic acid 1-methyl ester
• CAS No.: 175452-89-8
• Molecular Formula: C21H21NO6
• Molecular Weight: 383.39500
• Mol file: 175452-89-8.mol

Synonyms:

Chemical Property of N-Fmoc-D-Glutamic acid 1-methyl ester

Chemical Property:

• PSA: 101.93000
• LogP: 3.32240

Purity/Quality:

97% ^*data from raw suppliers

Fmoc-D-Glu-OMe 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of N-Fmoc-D-Glutamic acid 1-methyl ester

There total 2 articles about N-Fmoc-D-Glutamic acid 1-methyl 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: 81.0%

α-methyl γ-allyl (2R)-N-(fluoren-9-ylmethoxycarbonyl)glutamate (368443-68-9) → α-methyl (2R)-N-(fluoren-9-ylmethoxycarbonyl)glutamate ester (175452-89-8)

Guidance literature:

With phenylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1039/b100401h

Reference yield:

γ-allyl (2R)-N-(fluoren-9-ylmethoxycarbonyl)glutamate (204251-33-2) → α-methyl (2R)-N-(fluoren-9-ylmethoxycarbonyl)glutamate ester (175452-89-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / diethyl ether / 1 h / 0 °C

2: 81 percent / PhSiH₃ / (Ph₃P)4Pd⁽⁰⁾ / CH₂Cl₂ / 2 h / 20 °C

With phenylsilane; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In diethyl ether; dichloromethane;

DOI:10.1039/b100401h

Reference yield:

α-methyl (2R)-N-(fluoren-9-ylmethoxycarbonyl)glutamate ester (175452-89-8) → cyclo[-β-Ala-(2R)-Glu-α-OMe-γ-(2S)-Pro-(2R)-Asp-α-OMe-β-(2S)-Phe-]

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / aq. K₂CO₃ / diethyl ether / 1 h / 0 °C

2: 72 percent / PhSiH₃ / (Ph₃P)4Pd⁽⁰⁾ / CH₂Cl₂

3: 83 percent / piperidine / dimethylformamide / 0.75 h / 20 °C

4: PyBOP; DIPEA / dimethylformamide / 168 h / 20 °C

With piperidine; phenylsilane; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; potassium carbonate; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1039/b100401h

upstream raw materials:

α-methyl γ-allyl (2R)-N-(fluoren-9-ylmethoxycarbonyl)glutamate

γ-allyl (2R)-N-(fluoren-9-ylmethoxycarbonyl)glutamate

Downstream raw materials:

(2S)-phenylalanyl-β-alanyl-[α-methyl (2R)-glutamyl]-γ-(2S)-prolyl-[α-methyl (2R)-aspartate] diester

cyclo[-(2S,3S,E)-2-methyl-3-phenylethenyl-3-aminopropanoyl-α-(R)-Glu-α-OMe-γ-Sar-(R)-Asp-α-OMe-β-(S)-Phe-]

cyclo[-(3R,E)-3-phenylethenyl-3-aminopropanoyl-α-(R)-Glu-α-OMe-γ-Sar-(R)-Asp-α-OMe-β-(S)-Phe-]

cyclo[-(2S,3S,E)-2-methyl-3-phenylethenyl-3-aminopropanoyl-β-(R)-Glu-α-OMe-γ-(S)-Pro-(R)-Asp-α-OMe-β-(S)-Phe-]