Fmoc-Glu-OtBu

Base Information

• Chemical Name: Fmoc-Glu-OtBu
• CAS No.: 84793-07-7
• Molecular Formula: C24H27NO6
• Molecular Weight: 425.481
• Hs Code.: 29224290
• European Community (EC) Number: 688-911-5
• UNII: XXH3RHN4GT
• DSSTox Substance ID: DTXSID80426921
• Nikkaji Number: J956.302D
• Wikidata: Q72478409
• Mol file: 84793-07-7.mol

Synonyms:Fmoc-Glu-OtBu;84793-07-7;FMOC-L-GLUTAMIC ACID 1-TERT-BUTYL ESTER;Fmoc-L-Glu-OtBu;Fmoc-Glu-O-t-Bu;(4S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2-methylpropan-2-yl)oxy]-5-oxopentanoic acid;(S)-4-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(tert-butoxy)-5-oxopentanoic acid;N-(9-Fluorenylmethoxycarbonyl)glutamic acid alpha-tert-butyl ester;(S)-4-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-tert-butoxy-5-oxopentanoic acid;MFCD00065648;(4S)-5-(tert-Butoxy)-4-([[(9H-fluoren-9-yl)methoxy]carbonyl]amino)-5-oxopentanoic acid;(4S)-5-(tert-butoxy)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5-oxopentanoic acid;Fmoc-Glu-Ot-Bu;XXH3RHN4GT;Fmoc-L-Glutamic acid alpha-tert-butyl ester;SCHEMBL1709129;DTXSID80426921;GOPWHXPXSPIIQZ-FQEVSTJZSA-N;HY-Y1166;AKOS015895611;AKOS015922846;AC-1157;AM81716;CS-W009149;n-fmoc-l-glutamic acid-1-t-butyl ester;AS-17414;Fmoc-L-glutamic acid |A-tert.butyl ester;PD197326;EN300-1080054;n-alpha-fmoc-l-glutamic acid alpha-t-butyl ester;N-alpha-fmoc-l-glutamic acid-alpha-t-butyl ester;A840926;J-300121;Q-101546;N-(9-Fluorenylmethoxycarbonyl)glutamic acid |A-tert-butyl ester;N-(9H-Fluoren-9-ylmethoxycarbonyl)glutamic acid 1-tert-butyl ester;N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-glutamic-acid-t-butyl ester;(4S)-5-tert-Butoxy-4-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-5-oxopentanoic acid;L-Glutamic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 1-(1,1-dimethylethyl) ester;(4S)-5-tert-Butoxy-4-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-pentanoic acid

Chemical Property of Fmoc-Glu-OtBu

Chemical Property:

• Melting Point: 78-80 °C
• Boiling Point: 638.1 °C at 760 mmHg
• PKA: 4.46±0.10(Predicted)
• Flash Point: 339.7 °C
• PSA: 101.93000
• Density: 1.232 g/cm³
• LogP: 4.49110
• Storage Temp.: Store at RT.
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 425.18383758
• Heavy Atom Count: 31
• Complexity: 635

Purity/Quality:

99% ^*data from raw suppliers

Fmoc-L-Glu-OtBu ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Fmoc-Glu-OtBu

There total 5 articles about Fmoc-Glu-OtBu 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%

(fluorenylmethoxy)carbonyl chloride (28920-43-6) + L-glutamic acid α-tert-butyl ester (45120-30-7) → Fmoc-Glu-OtBu (84793-07-7)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; water; at 0 - 20 ℃; for 16h;

Reference yield: 85.0%

L-glutamic acid α-tert-butyl ester (45120-30-7) + N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) → Fmoc-Glu-OtBu (84793-07-7)

Guidance literature:

With sodium carbonate; In 1,4-dioxane; at 24 ℃; for 20h;

DOI:10.1021/jm00164a038

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) + 9-fluorenylmethyl N-succinimidyl carbonate (102774-86-7) + isobutene (115-11-7,15220-85-6) → Fmoc-Glu-OtBu (84793-07-7) + Fmoc-Glu(OtBu)-OH (71989-18-9) + N-(9-fluorenylmethoxycarbonyl)glutamic acid di-tert-butyl ester (129460-14-6)

Guidance literature:

With sodium carbonate; toluene-4-sulfonic acid; Yield given. Multistep reaction. Yields of byproduct given; 1) dioxane, gas pressure: 350 mbar, 3 d, r.t., 2) dioxane, 0 deg C to r.t., 14 h;

DOI:10.1055/s-1990-26943

upstream raw materials:

L-glutamic acid α-tert-butyl ester

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide

L-glutamic acid

9-fluorenylmethyl N-succinimidyl carbonate

Downstream raw materials:

(2S)-N₂-(9-fluorenylmethyloxycarbonyl)-glutamic acid α-tert-butyl ester γ-N-hydroxysuccinimide ester

2-(9H-fluoren-9-ylmethoxycarbonylamino)-4-{2-[(4-methoxy-phenyl)-diphenyl-methylsulfanyl]-ethylcarbamoyl}-butyric acid tert-butyl ester

C₄₉H₅₄N₂O₅S

Refernces

• 1、 -. "LIGAND-THERAPEUTIC AGENT CONJUGATES, SILICON-BASED LINKERS, AND METHODS FOR MAKING AND USING THEM". Paragraph 0373; 0374. . Retrieved 2014/09/29.
• 2、 Abraham,Nair,Kisliuk,Gaumont,Galivan. "Folate analogues. 33. Synthesis of folate and antifolate poly-γ-glutamates by [(9-fluorenylmethoxy)oxy]carbonyl chemistry and biological evaluation of certain methotrexate polyglutamate polylysine conjugates as inhibitors of the growth of H35 hepatoma cel". . p. 711 - 717. Retrieved 2007/10/02.