Fmoc-Glu(OAll)-OH

Base Information

• Chemical Name: Fmoc-Glu(OAll)-OH
• CAS No.: 133464-46-7
• Molecular Formula: C23H23 N O6
• Molecular Weight: 409.439
• Hs Code.: 2924 29 70
• DSSTox Substance ID: DTXSID50427066
• Nikkaji Number: J2.203.505C
• Wikidata: Q72478390
• Mol file: 133464-46-7.mol

Synonyms:Fmoc-Glu(OAll)-OH;133464-46-7;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-5-(allyloxy)-5-oxopentanoic acid;Fmoc-L-glutamic acid 5-allyl ester;(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-oxo-5-prop-2-enoxypentanoic acid;MFCD00190879;(S)-2-((((9H-Fluoren-9-yl)methoxy)carbonyl)-amino)-5-(allyloxy)-5-oxopentanoic acid;Fmoc-Glu(OAl)-OH;5-Allyl N-Fmoc-L-glutamate;SCHEMBL119481;DTXSID50427066;AMY30897;AKOS015839104;AKOS015895486;AC-8591;CS-W011681;FD21368;HY-W010965;N-Fmoc-L-glutamic Acid 5-Allyl Ester;AS-17651;Fmoc-Glu(OAll)-OH, >=96.0% (HPLC);M06243;EN300-1644759;J-006387;5-Allyl N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamate;N-(9H-Fluorene-9-ylmethoxycarbonyl)-L-glutamic acid 5-allyl ester;N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-L-glutamic Acid 5-Allyl Ester;N-alpha-(9-Fluorenylmethyloxycarbonyl)-L-glutamic-acid-beta allyl ester;(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-(allyloxy)-5-oxopentanoic acid;(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-5-oxo-5-(prop-2-en-1-yloxy)pentanoic acid

Chemical Property of Fmoc-Glu(OAll)-OH

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 8.69E-18mmHg at 25°C
• Melting Point: 122 - 128ºC
• Refractive Index: 1.585
• Boiling Point: 650.1oC at 760 mmHg
• PKA: 3.70±0.10(Predicted)
• Flash Point: 347oC
• PSA: 101.93000
• Density: 1.264g/cm3
• LogP: 3.87860
• Storage Temp.: 2-8°C
• Solubility.: soluble in Methanol
• 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)-OH ^*data from reagent suppliers

Safty Information:

• Statements: 22/22-36/37/38
• Safety Statements: 22-24/25-44-35-28-7-4

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of Fmoc-Glu(OAll)-OH

There total 4 articles about Fmoc-Glu(OAll)-OH 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: 98.0%

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide (82911-69-1) + (S)-2-amino-5-(allyloxy)-5-oxopentanoic acid hydrochloride → (S)-2-[((9H-fluoren-9-yl)methoxy)carbonylamino]-5-(allyloxy)-5-oxopentanoic acid (133464-46-7)

Guidance literature:

(S)-2-amino-5-(allyloxy)-5-oxopentanoic acid hydrochloride; With potassium carbonate; In water; at 0 ℃; for 0.333333h;

N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide; In 1,4-dioxane; water; at 20 ℃; for 8h; Further stages.;

DOI:10.1002/anie.200603209

Reference yield: 78.0%

C26H27NO6 (1159497-09-2) → (S)-2-[((9H-fluoren-9-yl)methoxy)carbonylamino]-5-(allyloxy)-5-oxopentanoic acid (133464-46-7)

Guidance literature:

With Alcalase-cross-linked-enzyme-aggregates; In tert-butyl alcohol; at 37 ℃; for 16h; pH=7.5; regioselective reaction; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1016/j.tetlet.2009.03.130

Reference yield:

L-glutamic acid (56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → (S)-2-[((9H-fluoren-9-yl)methoxy)carbonylamino]-5-(allyloxy)-5-oxopentanoic acid (133464-46-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / Me₃SiCl

2: 84 percent / Na₂CO₃ / H₂O; dioxane / Ambient temperature

With chloro-trimethyl-silane; sodium carbonate; In 1,4-dioxane; water;

DOI:10.1039/a800759d

upstream raw materials:

(fluorenylmethoxy)carbonyl chloride

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

L-glutamic acid

C₂₆H₂₇NO₆

Downstream raw materials:

N^α-decanoyl-L-glutamic acid

Refernces

• 1、 Mittapalli, Gopi Kumar,Osornio, Yazmin M.,Guerrero, Miguel A.,Reddy, Kondreddi Ravinder,Krishnamurthy, Ramanarayanan,Eschenmoser, Albert. "Mapping the landscape of potentially primordial informational oligomers: Oligodipeptides tagged with 2,4-disubstituted 5-aminopyrimidines as recognition elements". . p. 2478 - 2484. Retrieved 2008/03/11.
• 2、 Booth, Susan,Wallace, Emma N. K.,Singhal, Kavita,Bartlett, Philip N.,Kilburn, Jeremy D.. "Synthesis and electrochemical properties of tetrathiafulvalene derived amino acids and peptides". . p. 1467 - 1474. Retrieved 2007/10/03.