Fmoc-Asp-OAll CAS 144120-53-6
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 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 |
| pka | 4.09±0.19(Predicted) |
| form | Powder |
| color | White |
| Optical Rotation | [α]20/D 24.5±2°, c = 1% in DMF |
| BRN | 5460108 |
| Major Application | peptide synthesis |
| InChI | 1S/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 |
| InChIKey | ZJMVIWUCCRKNHY-IBGZPJMESA-N |
| SMILES | OC(=O)C[C@H](NC(=O)OCC1c2ccccc2-c3ccccc13)C(=O)OCC=C |
| 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 |
| Storage Class | 11 - Combustible Solids |
| 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 | 144120-52-5 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 |
Fmoc-Asp-OAll Preparation Products And Raw materials
| Raw materials | L-Aspartic acid, N-[(9H-fluoren-9-ylmethoxy)carbonyl]-, 4-(1,1-dimethylethyl) 1-(2-propen-1-yl) ester-->Trifluoroacetic acid-->Dichloromethane |
