(R)-(+)-2-Tetrahydrofuroic acid

Base Information

• Chemical Name: (R)-(+)-2-Tetrahydrofuroic acid
• CAS No.: 87392-05-0
• Molecular Formula: C5H8O3
• Molecular Weight: 116.117
• Hs Code.: DERIVATION
• European Community (EC) Number: 627-523-2
• UNII: 7396HFQ44J
• Nikkaji Number: J817.339G
• Wikidata: Q27094016
• Metabolomics Workbench ID: 147591
• Mol file: 87392-05-0.mol

Synonyms:87392-05-0;(R)-(+)-2-Tetrahydrofuroic acid;(r)-tetrahydrofuran-2-carboxylic acid;(R)-(+)-Tetrahydro-2-furoic acid;(R)-(+)-Tetrahydrofuran-2-carboxylic Acid;(r)-2-tetrahydrofuroic acid;(2R)-oxolane-2-carboxylic acid;2-Furancarboxylic acid, tetrahydro-, (2R)-;(r)-tetrahydro-2-furoic acid;(S)-2-Tetrahydrofuroic acid;(R)-(+)-2-Tetrahydrofuroicacid;(R)-2-Tetrahydrofuranoic acid;Tetrahydro-2-furoic acid, (+)-;D-Tetrahydro-furan-2-carboxylic acid;r-tetrahydro-2-furoic acid;7396HFQ44J;MFCD00211271;UNII-7396HFQ44J;tetrahydro-furan-2-carboxylic acid;r-thfc;SCHEMBL353229;(+)-tetrahydro-2-furoic acid;(R)-(+)-tetrahydrofuroic acid;UJJLJRQIPMGXEZ-SCSAIBSYSA-N;(R)-(+)tetrahydro-2-furoic acid;(r)-2-tetrahydrofurancarboxylic acid;(R)tetrahydrofuran-2-carboxylic acid;AKOS006240057;AKOS015855820;AC-3416;AC-3417;CS-W005223;DB03051;HY-W005223;(2r)-tetrahydro-2-furancarboxylic acid;(R)-tetrahydro-furan-2-carboxylic acid;(R)-tetrahydrofuran- 2-carboxylic acid;(2R)-tetrahydrofuran-2-ylcarboxylic acid;(r)-(+)-2-carboxy-tetrahydrofuroic acid;AS-12435;(r)-(+)-tetrahydro-2-furancarboxylic acid;(R)-(+)-Tetrahydro-2-furoic acid, 99%;(R)-(-)-tetrahydrofuran-2-carboxylic acid;AM20110255;T1740;EN300-116234;A842120;Q-200029;Q27094016

Chemical Property of (R)-(+)-2-Tetrahydrofuroic acid

Chemical Property:

• Appearance/Colour: clear to pale yellow liquid
• Vapor Pressure: 0.0107mmHg at 25°C
• Melting Point: 128-129ºC 13 mm Hg(lit.)
• Refractive Index: 1.459
• Boiling Point: 243.2 °C at 760 mmHg
• PKA: 3.60±0.20(Predicted)
• Flash Point: 113.2 °C
• PSA: 46.53000
• Density: 1.262 g/cm³
• LogP: 0.25000
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 99.8

Purity/Quality:

98.5%min ^*data from raw suppliers

(R)-(+)-2-TetrahydrofuroicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C,Xi
• Hazard Codes: C,Xi
• Statements: 22-34-36/37/38
• Safety Statements: 26-36/37/39-45-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(OC1)C(=O)O
• Isomeric SMILES: C1C[C@@H](OC1)C(=O)O
• Chemical Composition and Structure: (R)-Tetrahydrofuran-2-carboxylic acid, also known as (R)-(+)-2-Tetrahydrofuroic acid, has the molecular structure of a tetrahydrofuran ring with a carboxylic acid functional group.
• Uses: Classified as a chiral building block and an intermediate for pharmaceutical synthesis. Utilized as a chiral building block for the synthesis of furopenem, a clinically efficacious non-natural β-lactam antibiotic.^[1]
• History: First incorporated into pharmaceutical synthesis in the mid-1980s as a key intermediate for furopenem.
• Production Methods: Enzyme-catalyzed enantioselective hydrolysis of esters to produce (R)-Tetrahydrofuran-2-carboxylic acid.^[2]
• References: [1] A scalable chemoenzymatic preparation of (R)-tetrahydrofuran-2-carboxylic acid; DOI 10.1016/S0957-4166(03)00249-0; [2] There's No Industrial Biocatalyst Like Hydrolase:? Development of Scalable Enantioselective Processes Using Hydrolytic Enzymes; DOI 10.1021/op034014b

Technology Process of (R)-(+)-2-Tetrahydrofuroic acid

There total 15 articles about (R)-(+)-2-Tetrahydrofuroic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 86.0%

tetrahydrofuran-2-yl-[(S)-2-(hydroxydiphenylmethyl)pyrrolidin-1-yl]-methanone (1152061-22-7) → (R)-tetrahydro-2-furoic acid (87392-05-0)

Guidance literature:

With hydrogenchloride; water; at 90 ℃; for 20h;

DOI:10.1055/s-0028-1087532

Reference yield: 78.0%

(S)-3-Methyl-2-[((R)-tetrahydro-furan-2-carbonyl)-amino]-butyric acid methyl ester → (R)-tetrahydro-2-furoic acid (87392-05-0)

Guidance literature:

With hydrogenchloride; zinc(II) chloride; at 100 ℃; for 96h;

Reference yield: 29.0%

→ (R)-tetrahydro-2-furoic acid (87392-05-0)

Guidance literature:

upstream raw materials:

Tetrahydrofurfuryl alcohol

tetrahydro-2-furancarboxylic acid

methyl tetrahydrofuran-2-carboxylate

ethyl tetrahydrofurancarboxylate

Downstream raw materials:

(R)-(tetrahydrofuran-2-yl)methanol

N-propargyl-(R)-(+)-tetrhydro-2-furoic amide

(R)-tetrahydrofuran-2-carboxaldehyde

(S)-(+)-2-ethyltetrahydrofuran

Refernces

• 1、 Uyanik, Muhammet,Hayashi, Hiroki,Iwata, Hirokazu,Ishihara, Kazuaki. "Chiral ammonium hypoiodite salt-catalyzed enantioselective oxidative cycloetherification to 2-acyl tetrahydrofurans". . p. 353 - 355. Retrieved 2016/05/09.
• 2、 Fujima, Yoshito,Hirayama, Yoshihiro,Ikunaka, Masaya,Nishimoto, Yukifumi. "A scalable chemoenzymatic preparation of (R)-tetrahydrofuran-2-carboxylic acid". . p. 1385 - 1391. Retrieved 2007/10/03.