(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID

(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Property

Melting point:

71-73 °C (lit.)

Boiling point:

165-167 °C/0.3 mmHg (lit.)

alpha 

-14°(D/20℃) (c=5, メタノール)

Density 

1.3985 (rough estimate)

refractive index 

1.5800 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

pka

3.11±0.20(Predicted)

Appearance

White to light yellow Solid

optical activity

[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

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36

WGK Germany 

3

HS Code 

29321900

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P271Use only outdoors or in a well-ventilated area.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

(R)-(-)-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID Chemical Properties,Usage,Production

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