| Identification | More | [Name]
(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID | [CAS]
53558-93-3 | [Synonyms]
D-5-OXO-2-TETRAHYDROFURANCARBOXYLIC ACID (R-)
(R)-(-)-5-OXO-2-TETRAHYDROFURANCARBOXYLIC ACID
(R)-(-)-5-OXO-2-TETRAHYDROFUROIC ACID
(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
(R)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID
(R)-(-)-GAMMA-CARBOXY-GAMMA-BUTYROLACTONE
(R)-GAMMA-CARBOXY-GAMMA-BUTYROLACTONE
(R)-(-)-TETRAHYDRO-5-OXO-2-FURANECARBOXYLIC ACID
(theta)-2-furancarboxylicaci
(R)-(-)-5-OXO-2-TETRAHYDROFURANCARBOXYLI C ACID, 98% (97% EE/GLC)
(R)-5-Oxotetrahydro-2-furancarboxylic acid
(R)-5-OXOTETRAHYDRO-2-FURANCARBOXYLIC ACID 98+%
(R)-(-)-5-Oxo-2-tetrahydrofurancarboxylic acid, 99% (99% ee)
(r)-γ-carboxy-γ-butyrolactone
5-oxo-2-tetrahydrofurancarboxylic acid
(R)-γ-Carboxy-γ-butyrolactone, (R)-5-Oxotetrahydro-2-furancarboxylic acid
(R)-(-)-5-Oxo-2-tetrahydrofurancarboxylic acid, 99%, ee:.99%
(2R)-5-Oxooxolane-2β-carboxylic acid
(R)-Tetrahydro-5-oxo-2β-furancarboxylic acid | [Molecular Formula]
C5H6O4 | [MDL Number]
MFCD00011567 | [Molecular Weight]
130.1 | [MOL File]
53558-93-3.mol |
| Chemical Properties | Back Directory | [Appearance]
white crystalline powder | [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 | [form ]
solid | [pka]
3.11±0.20(Predicted) | [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) |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S36:Wear suitable protective clothing . | [WGK Germany ]
3
| [HS Code ]
29321900 |
| Hazard Information | Back Directory | [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 |
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