N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-D-GLUTAMIC ACID

Base Information

• Chemical Name: N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-D-GLUTAMIC ACID
• CAS No.: 104091-09-0
• Molecular Formula: C20H19 N O6
• Molecular Weight: 369.374
• Hs Code.: 2924299090
• Mol file: 104091-09-0.mol

Synonyms:D-Fmoc-glutamicacid; N-FMOC-D-glutamic acid

Chemical Property of N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-D-GLUTAMIC ACID

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 19 ° (C=1, DMF)
• Boiling Point: 635.785oC at 760 mmHg
• PKA: 3.72±0.10(Predicted)
• Flash Point: 338.311oC
• PSA: 116.42000
• Density: 1.366g/cm3
• LogP: 3.04750
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-D-glutamic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-Fmoc-D-glutamic acid is an N-Fmoc-protected form of D-Glutamic acid (G596960). D-Glutamic Acid is the unnatural (R)-enantiomer of Glutamic Acid, a non-essential amino acid. Its salt form (glutamate) is an important neurotransmitter that plays a key role in long-term potentiation and is important for learning and memory. Glutamic Acid is also a key molecule in cellular metabolism.

Technology Process of N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-D-GLUTAMIC ACID

There total 18 articles about N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-D-GLUTAMIC 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: 95.0%

Fmoc-Glu(OtBu)-OH (71989-18-9) → (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid (104091-09-0,136083-74-4,121343-82-6)

Guidance literature:

With water; for 24h; Flow reactor;

DOI:10.1002/anie.201909424

Reference yield: 85.0%

→ (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid (104091-09-0,136083-74-4,121343-82-6)

Guidance literature:

Reference yield: 83.0%

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + 1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole (1131148-55-4) → (S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid (104091-09-0,136083-74-4,121343-82-6)

Guidance literature:

With triethylamine; In water; acetonitrile; at 20 ℃; for 2h;

DOI:10.1055/s-0030-1261160

upstream raw materials:

Fmoc-Glu(OtBu)-OH

(S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-methoxy-5-oxopentanoic acid

L-glutamic acid

1-[(9-fluorenylmethyloxycarbonyl)]benzotriazole

Refernces

• 1、 Ibrahim, Tarek S.,Tala, Srinivasa R.,El-Feky, Said A.,Abdel-Samii, Zakaria K.,Katritzky, Alan R.. "Benzotriazole reagents for the syntheses of Fmoc-, Boc-, and Alloc-protected amino acids". . p. 2013 - 2016. Retrieved 2011.
• 2、 Villaverde, Gonzalo,Alfranca, Arantzazu,Gonzalez-Murillo, áfrica,Melen, Gustavo J.,Castillo, Rafael R.,Ramírez, Manuel,Baeza, Alejandro,Vallet-Regí, María. "Molecular Scaffolds as Double-Targeting Agents For the Diagnosis and Treatment of Neuroblastoma". . p. 3067 - 3072. Retrieved 2019.
• 3、 Palladino, Pasquale,Stetsenko, Dmitry A.. "New TFA-free cleavage and final deprotection in Fmoc solid-phase peptide synthesis: Dilute HCl in fluoro alcohol". . p. 6346 - 6349. Retrieved 2012.
• 4、 Minta, Ewelina,Boutonnet, Cédric,Boutard, Nicolas,Martinez, Jean,Rolland, Valérie. "Easy saponification by metal silanolates: Application in SPPS and in (S)-5-hydroxynorvaline preparation". . p. 1795 - 1797. Retrieved 2005.
• 5、 -. "Preparation method of N-fluorenylmethoxycarbonyl-gamma-(S-triphenylmethyl-cysteamine)-L-glutamic acid". Paragraph 0051. . Retrieved 2020/10/05.