Fmoc-Glu-OAll

Base Information

• Chemical Name: Fmoc-Glu-OAll
• CAS No.: 144120-54-7
• Molecular Formula: C23H23 N O6
• Molecular Weight: 409.439
• Hs Code.: 2924 29 70
• European Community (EC) Number: 852-966-5
• DSSTox Substance ID: DTXSID90427262
• Nikkaji Number: J1.552.370K
• Wikidata: Q72478392
• Mol file: 144120-54-7.mol

Synonyms:Fmoc-Glu-OAll;144120-54-7;Fmoc-Glu-allyl ester;(4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-prop-2-enoxypentanoic acid;Fmoc-L-glutamic acid |A-allyl ester;Fmoc-L-glutamic acid 1-allyl ester;1-Allyl N-Fmoc-L-glutamate;MFCD00467718;(S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid;Fmoc-Glu-OAl;SCHEMBL10173082;DTXSID90427262;ORKKMGRINLTBPC-FQEVSTJZSA-N;AKOS015839131;AKOS015908508;AC-8590;AM81715;CS-W008475;DS-8184;FD21376;HY-W008475;N-Fmoc-L-glutamic Acid 1-Allyl Ester;L-Glutamic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 1-(2-propen-1-yl) ester;Fmoc-Glu-OAll, >=99.0% (HPLC);F-6978;M06240;1-Allyl N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamate;N-(9H-Fluorene-9-ylmethoxycarbonyl)-L-glutamic acid 1-allyl ester;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamic Acid 1-Allyl Ester;(S)-4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-(allyloxy)-5-oxopentanoic acid;N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-glutamic-acid-alpha allyl ester (Fmoc-L-Glu-OAll)

Chemical Property of Fmoc-Glu-OAll

Chemical Property:

• Appearance/Colour: White to off white powder
• Vapor Pressure: 6.64E-18mmHg at 25°C
• Melting Point: 118-122 °C
• Boiling Point: 652.3oC at 760 mmHg
• PKA: 4.46±0.10(Predicted)
• Flash Point: 348.3oC
• PSA: 101.93000
• Density: 1.264g/cm3
• LogP: 3.87860
• Storage Temp.: 2-8°C
• Solubility.: soluble in Dimethylformamide
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 11
• Exact Mass: 409.15253745
• Heavy Atom Count: 30
• Complexity: 613

Purity/Quality:

≥98%,≥99%, ^*data from raw suppliers

Fmoc-glu-oall ^*data from reagent suppliers

Safty Information:

• Safety Statements: 22-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C=CCOC(=O)C(CCC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: C=CCOC(=O)[C@H](CCC(=O)O)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Uses: Allyl esters are useful carboxy protecting groups in the synthesis of various cyclic peptides glycopeptides. Allyl esters are cleaved quantitatively under mild conditions using Pd(0) catalyst. Fmoc-glu-oall, is an amino acid derivative used in chemical synthesis and peptide chemistry.

Technology Process of Fmoc-Glu-OAll

There total 3 articles about Fmoc-Glu-OAll 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: 89.0%

(S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid (104091-09-0,136083-74-4,121343-82-6) + allyl alcohol (107-18-6) → Nα-(9-fluorenylmethoxycarbonyl)-L-glutamic acid α-allyl ester (144120-54-7)

Guidance literature:

With CLEA-Alcalase; In tert-butyl methyl ether; at 50 ℃; for 16h; Molecular sieve;

DOI:10.1055/s-0028-1083362

Reference yield: 80.0%

4-(1,1-dimethylethyl) ester of Nα-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-glutamic acid allyl ester → Nα-(9-fluorenylmethoxycarbonyl)-L-glutamic acid α-allyl ester (144120-54-7)

Guidance literature:

With zinc dibromide; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1021/jo0491206

Reference yield:

Fmoc-Glu(OtBu)-OH (71989-18-9) → Nα-(9-fluorenylmethoxycarbonyl)-L-glutamic acid α-allyl ester (144120-54-7)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N'-dicyclohexylcarbodiimide / tetrahydrofuran

2: CF₃CO₂H / CH₂Cl₂ / 0.5 h

With dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1016/0040-4039(93)85003-F

upstream raw materials:

Fmoc-Glu(OtBu)-OH

(S)-2-[{({9H-fluoren-9-yl}methoxy)carbonyl}amino]pentanedioic acid

allyl alcohol

Downstream raw materials:

2-(9H-fluoren-9-ylmethoxycarbonylamino)-pentanedioic acid 1-allyl ester 5-(9-phenyl-9H-fluoren-9-yl) ester

(S)-4-Acetylamino-4-(4-nitro-phenylcarbamoyl)-butyric acid

Refernces

• 1、 Dao, Yuankun,Han, Lin,Wang, Hanxuan,Dong, Suwei. "α-Selective Lysine Ligation and Application in Chemical Synthesis of Interferon Gamma". . . Retrieved 2019.
• 2、 Treder, Adam P.,Hickey, Jennifer L.,Tremblay, Marie-Claude J.,Zaretsky, Serge,Scully, Conor C. G.,Mancuso, John,Doucet, Annie,Yudin, Andrei K.,Marsault, Eric. "Solid-phase parallel synthesis of functionalised medium-to-large cyclic peptidomimetics through three-component coupling driven by aziridine aldehyde dimers". . p. 9249 - 9255. Retrieved 2015/06/16.