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

form 

Powder

pka

4.09±0.19(Predicted)

color 

White

optical activity

[α]20/D 24.5±2°, c = 1% in DMF

BRN 

5460108

CAS DataBase Reference

144120-53-6(CAS DataBase Reference)

Safety Information

Safety Statements 

22-24/25

WGK Germany 

3

HS Code 

2924 29 70

HazardClass 

IRRITANT

MSDS

• Language:English Provider:SigmaAldrich

Fmoc-Asp-OAll Usage And Synthesis

Chemical Properties

White crystalline powder

Uses

Fmoc-asp-oall is an intermediate used in the synthesis of some biologically active molecules.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

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

Fmoc-Asp-OAll(144120-53-6)Related Product Information

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