Fmoc-L-glutamic acid 5-tert-butyl ester

Fmoc-L-glutamic acid 5-tert-butyl ester Basic information
Product Name:Fmoc-L-glutamic acid 5-tert-butyl ester
Synonyms:N-ALPHA-FMOC-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER;N-ALPHA-FMOC-L-GLUTAMIC ACID GAMMA-TERT-BUTYL ESTER;N-9-FLUORENYLMETHYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER;N-9-FLUORENYLMETHYLOXYCARBONYL-L-GLUTAMIC ACID GAMMA-TERT-BUTYL ESTER;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-GLUTAMIC-ACID-GAMMA-T-BUTYL ESTER;N-ALPHA-(9-FLUORENYLMETHOXYCARBONYL)-GAMMA-T-BUTYL-L-GLUTAMIC ACID;N-FMOC-L-GLUTAMIC ACID GAMMA-T-BUTYL ESTER;N-FMOC-O-T-BUTYL-L-GLU
CAS:71989-18-9
MF:C24H27NO6
MW:425.47
EINECS:276-253-8
Product Categories:Fmoc-Amino acid series;Fmoc-Amino Acids;Amino Acids;Glutamic acid [Glu, E];Fmoc-Amino Acids and Derivatives;Pyridines;Amino Acid Derivatives;Amino Acids (N-Protected);Biochemistry
Mol File:71989-18-9.mol
Fmoc-L-glutamic acid 5-tert-butyl ester Structure
Fmoc-L-glutamic acid 5-tert-butyl ester Chemical Properties
Melting point 83-90 °C
alpha -4.5 º (c=1, 80% acetic acid)
Boiling point 633.5±55.0 °C(Predicted)
density 1.232±0.06 g/cm3(Predicted)
refractive index -4 ° (C=1, 80% AcOH)
storage temp. Store below +30°C.
solubility soluble in Methanol
pka3.70±0.10(Predicted)
form powder to crystal
color White to Almost white
optical activity[α]20/D 5.0±2.0°, c = 1% in acetic acid: water (4:1)
BRN 3636375
InChIKeyOTKXCALUHMPIGM-FQEVSTJZSA-N
SMILESC(O)(=O)[C@H](CCC(OC(C)(C)C)=O)NC(OCC1C2=C(C=CC=C2)C2=C1C=CC=C2)=O
CAS DataBase Reference71989-18-9(CAS DataBase Reference)
Safety Information
Hazard Codes Xi
Risk Statements 36/37/38
Safety Statements 26-27-36/37/39-24/25
WGK Germany 3
HS Code 2924 29 70
MSDS Information
ProviderLanguage
Fmoc-Glu(OtBu)-OH English
SigmaAldrich English
Fmoc-L-glutamic acid 5-tert-butyl ester Usage And Synthesis
DescriptionFmoc-L-glutamic acid 5-tert-butyl ester is a Fmoc derivative with an N-substituted tert-butyl ester molecule. It is white or gray-white solid crystals at room temperature and pressure, poor solubility in water and insoluble in petroleum ether, but soluble in ethyl acetate, acetic acid and N,N-dimethylformamide.
Chemical PropertiesWhite powder
UsesFmoc-Glu(OtBu)-OH (Fmoc-L-glutamic acid 5-tert-butyl ester) can be employed as a:
  • Ligand in the synthesis of cis-substituted cyclopropane carboxylic acids via C-H activation of cyclopropane carboxamides using Pd catalyst.
  • Linker in the preparation of multi-small molecule-conjugated PTX (paclitaxel) derivatives.

It can be also used as a building block in the preparation of stapled α-helical peptides , and peptide C-terminal thioesters .
General DescriptionThe product number for this product was previously 04-12-1020.

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