(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID manufacturers
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| | (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Basic information |
| | (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Chemical Properties |
| Melting point | 71-73 °C (lit.) | | alpha | -14°(D/20℃) (c=5, メタノール) | | Boiling point | 165-167 °C/0.3 mmHg (lit.) | | density | 1.3985 (rough estimate) | | refractive index | 1.5800 (estimate) | | storage temp. | Inert atmosphere,Room Temperature | | pka | 3.11±0.20(Predicted) | | form | solid | | Appearance | White to light yellow Solid | | Optical Rotation | [α]20/D 14°, c = 5 in methanol | | BRN | 1424499 | | InChI | InChI=1S/C5H6O4/c6-4-2-1-3(9-4)5(7)8/h3H,1-2H2,(H,7,8)/t3-/m1/s1 | | InChIKey | QVADRSWDTZDDGR-GSVOUGTGSA-N | | SMILES | O1C(=O)CC[C@@H]1C(O)=O | | CAS DataBase Reference | 53558-93-3(CAS DataBase Reference) | | EPA Substance Registry System | 2-Furancarboxylic acid, tetrahydro-5-oxo-, (2R)- (53558-93-3) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36 | | WGK Germany | 3 | | TSCA | TSCA listed | | HS Code | 29321900 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Usage And Synthesis |
| Chemical Properties | white crystalline powder | | Uses | (R)-5-Oxotetrahydrofuran-2-carboxylic Acid is an intermediate used to synthesize 2'',3''-dideoxy-4''-selenonucleosides as potential antiviral agents. | | General Description | (R)-()-5-Oxo-2-tetrahydrofurancarboxylic acid belongs to the class of furans, considered as heterocyclic building blocks. It is used as an HPLC derivatization reagent for UV/Vis detection. | | Synthesis | Example 1: Synthesis of (R)-(-)-5-oxo-2-tetrahydrofuran carboxylic acid (2)
1. To a mixed solution of D-glutamic acid (1 , 25 g, 170 mmol) in water (67 mL) and concentrated hydrochloric acid (35 mL) was slowly added a solution of NaNO2 (17.5 g, 253.6 mmol) in water (37.5 mL) at 0 °C for 4 hours.
2. After the addition was completed, the reaction mixture was stirred overnight at room temperature to obtain a clarified solution.
3. The solvent was removed by vacuum evaporation and the residue was treated with ethyl acetate (EtOAc, 80 mL) and filtered.
4. The filtrate was dried over anhydrous sodium sulfate (Na2SO4) and subsequently concentrated.
5. The concentrated residue was crystallized from a solvent mixture of ethyl acetate/benzene/hexane to afford (R)-(-)-5-oxo-2-tetrahydrofuran carboxylic acid (2) as a white crystalline solid (12.63 g, 57% yield).
Product Characterization:
- Melting point: 71-73°C
- 1H NMR (400 MHz, CD3OD): δ 4.20 (m, 1H, CHO), 1.8-2.3 (m, 4H, CH2CH2). | | References | [1] Tetrahedron, 2006, vol. 62, # 37, p. 8687 - 8695
[2] Tetrahedron: Asymmetry, 1993, vol. 4, # 6, p. 1391 - 1396
[3] Organic Letters, 2014, vol. 16, # 16, p. 4336 - 4339
[4] Pharmazie, 1995, vol. 50, # 1, p. 15 - 21
[5] Patent: US2004/67877, 2004, A1 |
| | (R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Preparation Products And Raw materials |
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