Fmoc-L-Glu(tBu)-NH2

Base Information

• Chemical Name: Fmoc-L-Glu(tBu)-NH2
• CAS No.: 104090-92-8
• Molecular Formula: C₂₄H₂₈N₂O₅
• Molecular Weight: 424.497
• DSSTox Substance ID: DTXSID90451961
• Nikkaji Number: J1.081.164C
• Wikidata: Q82272282
• Mol file: 104090-92-8.mol

Synonyms:Fmoc-L-Glu(tBu)-NH2;104090-92-8;tert-butyl (4S)-5-amino-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxopentanoate;(S)-tert-Butyl 4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-amino-5-oxopentanoate;Fmoc-L-IsoGln-OtBu;DTXSID90451961;MFCD01632029;AKOS027340187;CS-0339687;E70587;(S)-2-(9H-Fluorene-9-ylmethoxycarbonylamino)-4-(tert-butoxycarbonyl)butyramide;Tert-butyl (S)-4-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-5-amino-5-oxopentanoate

Chemical Property of Fmoc-L-Glu(tBu)-NH2

Chemical Property:

• PSA: 107.72000
• LogP: 4.59370
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 10
• Exact Mass: 424.19982200
• Heavy Atom Count: 31
• Complexity: 637

Purity/Quality:

98.5% ^*data from raw suppliers

Fmoc-l-glu(tbu)-nh2 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)CCC(C(=O)N)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13
• Isomeric SMILES: CC(C)(C)OC(=O)CC[C@@H](C(=O)N)NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13

Technology Process of Fmoc-L-Glu(tBu)-NH2

There total 2 articles about Fmoc-L-Glu(tBu)-NH2 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: 99.0%

Fmoc-Glu(OtBu)-OH (71989-18-9) → Fmoc-L-E(γ-OtBu)-NH2 (104090-92-8)

Guidance literature:

Fmoc-Glu(OtBu)-OH; With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20 ℃; for 0.333333h;

With ammonia; In dichloromethane; water; for 1.5h; Further stages.;

DOI:10.1021/ol026463m

Reference yield:

Fmoc-Glu(t-Bu)-benzotriazolyl ester (124007-49-4) → Fmoc-L-E(γ-OtBu)-NH2 (104090-92-8)

Guidance literature:

With ammonia; In dichloromethane; at 0 ℃; for 1h; Yield given;

DOI:10.1021/jo00374a019

Reference yield:

Fmoc-L-E(γ-OtBu)-NH2 (104090-92-8) → 2-(1-{[2-(1-benzyloxycarbonylamino-5-tert-butoxycarbonylamino-pentyl)-oxazole-4-carbonyl]-amino}-3-tert-butoxycarbonyl-propyl)-thiazole-4-carboxylic acid ethyl ester (474686-25-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 100 percent / Lawesson's reagent / CH₂Cl₂

2.1: KHCO₃ / 1,2-dimethoxy-ethane / -40 - -20 °C

2.2: 94 percent / TFAA; 2,6-lutidine / 1,2-dimethoxy-ethane / -40 - -20 °C

3.1: 98 percent / piperidine / CH₂Cl₂ / 0.5 h / 20 °C

4.1: 98 percent / benzotriazol-1-yl-oxy-tris(dimethylamino) phosphonium PF₆; diisopropylethylamine / dimethylformamide / 5 h / 20 °C

With piperidine; Lawessons reagent; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; potassium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol026463m

upstream raw materials:

Fmoc-Glu(t-Bu)-benzotriazolyl ester

Fmoc-Glu(OtBu)-OH

Downstream raw materials:

2-(1-{[2-(1-benzyloxycarbonylamino-5-tert-butoxycarbonylamino-pentyl)-oxazole-4-carbonyl]-amino}-3-tert-butoxycarbonyl-propyl)-thiazole-4-carboxylic acid ethyl ester

C₈₈H₁₂₆N₂₀O₂₄

C₈₁H₁₁₆N₂₀O₂₄

C₈₁H₁₁₆N₂₀O₂₄

Refernces

• 1、 Wang, Bo,Lamattina, Joseph W.,Marshall, Savannah L.,Booker, Squire J.. "Capturing Intermediates in the Reaction Catalyzed by NosN, a Class C Radical S-Adenosylmethionine Methylase Involved in the Biosynthesis of the Nosiheptide Side-Ring System". supporting information. p. 5788 - 5797. Retrieved 2019/04/17.
• 2、 Singh, Yogendra,Stoermer, Martin J.,Lucke, Andrew J.,Glenn, Matthew P.,Fairlie, David P.. "Regioselective synthesis of antiparallel loops on a macrocyclic scaffold constrained by oxazoles and thiazoles". . p. 3367 - 3370. Retrieved 2007/10/03.