(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylacetic acid

Base Information

• Chemical Name: (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylacetic acid
• CAS No.: 111524-95-9
• Molecular Formula: C23H19NO4
• Molecular Weight: 373.408
• Hs Code.: 29242990
• European Community (EC) Number: 625-027-0
• Nikkaji Number: J1.149.853A
• Mol file: 111524-95-9.mol

Synonyms:163883-97-4;Fmoc-DL-phenylglycine;2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylacetic acid;(R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylacetic acid;2-(9H-fluoren-9-ylmethoxycarbonylamino)-2-phenylacetic acid;2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-phenylacetic acid;MFCD00155632;MFCD00190891;(R)-2-(Fmoc-amino)-2-phenylacetic acid;(S)-N-Fmoc-2-amino-2-phenylacetic Acid;2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}-2-phenylacetic acid;Fmoc-dl-phg-oh, AldrichCPR;SCHEMBL2307241;PCJHOCNJLMFYCV-UHFFFAOYSA-N;AKOS009156528;AB04141;AB04533;SY032420;SY032584;FT-0642482;FT-0652935;EN300-81098;F78661;N-(9H-Fluorene-9-ylmethoxycarbonyl)-2-phenylglycine;2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylaceticacid;2-(((9h-fluoren-9-yl)methoxy)carbonylamino)-2-phenylacetic acid;Benzeneacetic acid, alpha-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-

Chemical Property of (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylacetic acid

Chemical Property:

• Melting Point: 170-180°C
• Boiling Point: 606.3 °C at 760 mmHg
• PKA: 3.39±0.10(Predicted)
• Flash Point: 320.5 °C
• PSA: 75.63000
• Density: 1.299 g/cm³
• LogP: 4.74190
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 373.13140809
• Heavy Atom Count: 28
• Complexity: 537

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-d-phg-oh ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(=O)O)NC(=O)OCC2C3=CC=CC=C3C4=CC=CC=C24
• Uses: Fmoc-d-phg-oh, is an amino acid derivative used in peptide chemistry.

Technology Process of (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylacetic acid

There total 7 articles about (R)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-phenylacetic 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: 85.0%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-α-phenylglycine (69-91-0,875-74-1,2835-06-5,2935-35-5) → N-(9-Fluorenylmethyloxy)carbonyl-L-phenylglycine (102410-65-1,111524-95-9,163883-97-4)

Guidance literature:

Reference yield:

2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-2-phenylacetic acid (163883-97-4) → Fmoc-Phg-OH (102410-65-1,163883-97-4) + N-Fmoc-D-phenylglycine (111524-95-9,163883-97-4)

Guidance literature:

With trifluoroacetic acid; In hexane; isopropyl alcohol; at 25 ℃; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/bkcs.11694

Reference yield:

(R)-allyl-(N-9-fluorenylmethoxycarbonyl)phenylglycinate → N-Fmoc-D-phenylglycine (111524-95-9,163883-97-4)

Guidance literature:

With morpholine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 23 ℃; for 0.166667h;

DOI:10.1021/ol026660l

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

L-α-phenylglycine

2,5-dioxo-4-phenyl-oxazolidine-3-carboxylic acid 9H-fluoren-9-ylmethyl ester

(R)-phenylglycine

Downstream raw materials:

Phg-MePhe-Thz

Phg-MePhe-Thz-OTmse

(-)-(R)-(N-9-fluorenylmethoxycarbonyl)phenylglycinol

Fmoc-D-Phg-SH

Refernces

• 1、 Islam, Md. Fokhrul,Adhikari, Suraj,Paik, Man-Jeong,Lee, Wonjae. "Determination of Chemical and Enantiomeric Purity of α-Amino Acids and their Methyl Esters as N-Fluorenylmethoxycarbonyl Derivatives Using Amylose-derived Chiral Stationary Phases". . p. 332 - 338. Retrieved 2019/04/13.
• 2、 Bain,Wacker, Dean A.,Kuo, Eric E.,Chamberlin, A. Richard. "Site-specific incorporation of non-natural residues into peptides: Effect of residue structure on suppression and translation efficiencies". . p. 2389 - 2400. Retrieved 2007/10/02.