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Fmoc-Asp-OAll

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CAS:144120-53-6
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Fmoc-Asp-OAll Basic information
Product Name:Fmoc-Asp-OAll
Synonyms:Fmoc-L-aspartic acid a-allyl ester≥ 98% (HPLC);(9H-Fluoren-9-yl)MethOxy]Carbonyl Asp-OAll;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-ASPARTIC;(3S)-3-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-4-oxo-4-(prop-2-en-1-yloxy)butanoic acid;Fmoc-L-aspartic acid α-allyl ester;FMOC-ASP-OAI;FMOC-ASP-OAL;FMOC-ASP-OALL
CAS:144120-53-6
MF:C22H21NO6
MW:395.41
EINECS:276-252-2
Product Categories:Aspartic acid [Asp, D];Fmoc-Amino Acids and Derivatives;Fmoc-Amino acid series;amino acids
Mol File:144120-53-6.mol
Fmoc-Asp-OAll Structure
Fmoc-Asp-OAll Chemical Properties
Melting point 131.0 to 135.0 °C
Boiling point 634.8±55.0 °C(Predicted)
density 1.286±0.06 g/cm3(Predicted)
storage temp. 2-8°C
solubility Soluble in water or 1% acetic acid
pka4.09±0.19(Predicted)
form Powder
color White
Optical Rotation[α]20/D 24.5±2°, c = 1% in DMF
BRN 5460108
Major Applicationpeptide synthesis
InChI1S/C22H21NO6/c1-2-11-28-21(26)19(12-20(24)25)23-22(27)29-13-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18/h2-10,18-19H,1,11-13H2,(H,23,27)(H,24,25)/t19-/m0/s1
InChIKeyZJMVIWUCCRKNHY-IBGZPJMESA-N
SMILESOC(=O)C[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(=O)OCC=C
CAS DataBase Reference144120-53-6(CAS DataBase Reference)
Safety Information
Safety Statements 22-24/25
WGK Germany 3
HS Code 2924 29 70
HazardClass IRRITANT
Storage Class11 - Combustible Solids
MSDS Information
ProviderLanguage
SigmaAldrich English
Fmoc-Asp-OAll Usage And Synthesis
Chemical PropertiesWhite crystalline powder
UsesFmoc-asp-oall is an intermediate used in the synthesis of some biologically active molecules.
reaction suitabilityreaction type: Fmoc solid-phase peptide synthesis
Synthesis
L-Aspartic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 4-(1,1-dimethylethyl) 1-(2-propen-1-yl) ester

144120-52-5

Fmoc-Asp-OAll

144120-53-6

Procedure for the synthesis of Nα-Fmoc-L-aspartic acid α-allyl ester: Nα-Fmoc-L-aspartic acid (OH) allyl ester (0.77 g; 1.94 mmol) was dissolved in a mixture of dichloromethane (DCM, 4 ml) and trifluoroacetic acid (TFA, 2 ml), and the reaction was stirred for 1 h at room temperature. After completion of the reaction, the mixture was concentrated to dryness under reduced pressure. The resulting solid was dissolved in saturated aqueous sodium bicarbonate (NaHCO3) solution and washed with ether. Subsequently, it was acidified to pH 2 with 5% hydrochloric acid (HCl) to produce a white precipitate. It was extracted twice with ethyl acetate (EE) and the organic phases were combined. The organic phase was washed with acidified water (HCl, pH 1), dried over anhydrous sodium sulfate (Na2SO4), and evaporated under reduced pressure to afford the target product Nα-Fmoc-L-aspartic acid α-allyl ester (87% yield). The product was structurally confirmed by 1H NMR (250 MHz, DMSO-d6) and 13C NMR (75 MHz, CDCl3), and the purity was verified by ESI-MS (m + Na: 418.1) and HPLC (Rt: 22.0 min, gradient 10-100%).

References[1] Tetrahedron Letters, 1992, vol. 33, # 32, p. 4557 - 4560
[2] Chemical Communications, 2011, vol. 47, # 39, p. 10939 - 10941
[3] Carbohydrate Research, 2007, vol. 342, # 3-4, p. 541 - 557
[4] Journal of Medicinal Chemistry, 2011, vol. 54, # 21, p. 7648 - 7662
[5] Patent: US2014/39153, 2014, A1. Location in patent: Paragraph 0150; 0151; 0152
Tag:Fmoc-Asp-OAll(144120-53-6) Related Product Information
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