(S)-methyl 5-oxotetrahydrofuran-2-carboxylate

Base Information

• Chemical Name: (S)-methyl 5-oxotetrahydrofuran-2-carboxylate
• CAS No.: 21461-85-8
• Molecular Formula: C6H8O4
• Molecular Weight: 144.12500
• Hs Code.: 2932190090
• DSSTox Substance ID: DTXSID80451596
• Nikkaji Number: J633.324I
• Wikidata: Q82271686
• Mol file: 21461-85-8.mol

Synonyms:(S)-methyl 5-oxotetrahydrofuran-2-carboxylate;21461-85-8;METHYL (2S)-5-OXOOXOLANE-2-CARBOXYLATE;Methyl (S)-5-oxotetrahydrofuran-2-carboxylate;SCHEMBL21389240;DTXSID80451596;MFCD16039325;AKOS016014154;(S)-methyl5-oxotetrahydrofuran-2-carboxylate;CS-0336442;F83688;(s)-(+)-methyl tetrahydro-5-oxo-2-furancarboxylate;J-502496;(S)-5-Oxotetrahydrofuran-2-carboxylic acid methyl ester;(S)-2-METHYL-5-OXOTETRAHYDROFURAN-2-CARBOXYLIC ACID

Chemical Property of (S)-methyl 5-oxotetrahydrofuran-2-carboxylate

Chemical Property:

• PSA: 52.60000
• LogP: -0.13500
• Storage Temp.: 2-8°C
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 144.04225873
• Heavy Atom Count: 10
• Complexity: 163

Purity/Quality:

99.3% ^*data from raw suppliers

(S)-Methyl-5-oxotetrahydrofuran-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCC(=O)O1
• Isomeric SMILES: COC(=O)[C@@H]1CCC(=O)O1

Technology Process of (S)-methyl 5-oxotetrahydrofuran-2-carboxylate

There total 11 articles about (S)-methyl 5-oxotetrahydrofuran-2-carboxylate 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: 73.0%

methanol (67-56-1) + (2S)-tetrahydro-5-oxofuran-2-carboxylic acid (21461-84-7) → (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid methyl ester (21461-85-8)

Guidance literature:

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid; With thionyl chloride; for 4h; Heating;

methanol; With triethylamine; In dichloromethane; at 20 ℃; for 12h; Further stages.;

DOI:10.1002/jhet.5570440239

Reference yield:

dimethyl 2-ketoglutarate (13192-04-6) → (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid methyl ester (21461-85-8) + (R)-(-)-tetrahydro-5-oxo-2-furancarboxylic acid methyl ester (19684-04-9)

Guidance literature:

dimethyl 2-ketoglutarate; With 9-methoxy-10,11-dihydrocinchonidine; hydrogen; 5percent Pt/Al₂O₃; In acetic acid; at 20 ℃; under 750.075 Torr;

With toluene-4-sulfonic acid; In acetic acid; Further stages. Title compound not separated from byproducts.;

DOI:10.1039/b000390p

Reference yield:

(S)-5-Morpholin-4-yl-4-trimethylsilanyl-2,3-dihydro-furan-2-carboxylic acid methyl ester → (S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid methyl ester (21461-85-8)

Guidance literature:

With potassium hydrogen difluoride; In acetonitrile; at 23 ℃;

DOI:10.1021/ja025604c

upstream raw materials:

diazomethane

(2S)-tetrahydro-5-oxofuran-2-carboxylic acid

dimethyl 2-ketoglutarate

(+/-)-tetrahydro-5-oxo-2-furancarboxylic acid methyl ester

Downstream raw materials:

5-methyl (3S,5S)-3-acetylamino-2-oxotetrahydrofuran-5-carboxylate

5-methyl (3R,5S)-3-acetylamino-2-oxotetrahydrofuran-5-carboxylate

(S)-(+)-tetrahydro-5-oxo-2-furancarboxylic acid ethyl ester

Refernces

• 1、 Pirc, Samo,Recnik, Simon,Skof, Marko,Svete, Jurij,Golic, Ljubo,Meden, Anton,Stanovnik, Branko. "Synthesis of spirolactones by 1,3-dipolar cycloadditions to methyl (S)-3-[(E)-cyanomethylidene]-2-oxotetrahydrofuran-5-carboxylate". . p. 411 - 416. Retrieved 2002.
• 2、 Levy, Stuart G.,Jacques, Vincent,Zhou, Kevin Li,Kalogeropoulos, Shirley,Schumacher, Kelly,Amedio, John C.,Scherer, Jonathan E.,Witowski, Steven R.,Lombardy, Richard,Koppetsch, Karsten. "Development of a multigram asymmetric synthesis of 2-(R)-2-(4,7,10-tris tert-butylcarboxymethyl-1,4,7,10-tetraazacyclododec-1-yl)-pentanedioic acid, 1-tert-butyl ester, (R)-tert-Bu4-DOTAGA1". experimental part. p. 535 - 542. Retrieved 2010/04/22.