(S)-Tetrahydrofuran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (S)-Tetrahydrofuran-2-carboxylic acid methyl ester
• CAS No.: 87324-01-4
• Molecular Formula: C6H10O3
• Molecular Weight: 130.144
• Hs Code.: 2932190090
• UNII: TQP8Q54YKX
• Nikkaji Number: J1.907.779I
• Mol file: 87324-01-4.mol

Synonyms:87324-01-4;(S)-Tetrahydrofuran-2-carboxylic acid methyl ester;TQP8Q54YKX;(s)-methyl tetrahydrofuran-2-carboxylate;2-Furancarboxylic acid, tetrahydro-, methyl ester, (2S)-;Methyl (S)-tetrahydro-2-furancarboxylate;Methyl tetrahydro-2-furancarboxylate, (S)-;UNII-TQP8Q54YKX;SCHEMBL7016675;IXHZGHPQQTXOKV-YFKPBYRVSA-N;methyl (2S)-oxolane-2-carboxylate;AKOS006275213;methyl (2S)-tetrahydrofuran-2-carboxylate;(+)-(s)-methyl tetrahydrofuran-2-carboxylate

Chemical Property of (S)-Tetrahydrofuran-2-carboxylic acid methyl ester

Chemical Property:

• PSA: 35.53000
• LogP: 0.33840
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 111

Purity/Quality:

(S)-Tetrahydrofuran-2-carboxylicacidmethylester 95% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCCO1
• Isomeric SMILES: COC(=O)[C@@H]1CCCO1

Technology Process of (S)-Tetrahydrofuran-2-carboxylic acid methyl ester

There total 2 articles about (S)-Tetrahydrofuran-2-carboxylic acid methyl ester 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:

methyl tetrahydrofuran-2-carboxylate (37443-42-8) → (S)-(+)-methyl tetrahydrofuran-2-carboxylate (87324-01-4) + (S)-tetrahydro-2-furoic acid (87392-07-2) + (R)-tetrahydro-2-furoic acid (87392-05-0) + (R)-(-)-methyl tetrahydrofuran-2-carboxylate (87324-00-3)

Guidance literature:

With Aspergillus melleus protease; In phosphate buffer; at 20 ℃; for 2h; pH=7; Title compound not separated from byproducts;

DOI:10.1016/S0957-4166(03)00249-0

Reference yield:

diazomethane (186581-53-3,908094-01-9,334-88-3) + tetrahydro-2-furancarboxylic acid (16874-33-2) → (S)-(+)-methyl tetrahydrofuran-2-carboxylate (87324-01-4) + (R)-(-)-methyl tetrahydrofuran-2-carboxylate (87324-00-3)

Guidance literature:

In methanol; diethyl ether; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

Reference yield: 91.0%

(S)-(+)-methyl tetrahydrofuran-2-carboxylate (87324-01-4) + aniline (62-53-3) → (S)-N-phenyloxolane-2-carboxamide

Guidance literature:

With bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; 1,3-bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium; In toluene; at 140 ℃; for 16h; Glovebox; Inert atmosphere; Sealed tube;

DOI:10.1002/anie.201808560

upstream raw materials:

diazomethane

tetrahydro-2-furancarboxylic acid

methyl tetrahydrofuran-2-carboxylate

Downstream raw materials:

(S)-(tetrahydrofuran-2-yl)methanol

(S)-(+)-tetrahydrofuran-2-yl 2-<(2'-nitrophenyl)methylene>acetoacetate

(RS)-furnidipine

(SS)-furnidipine

Refernces

• 1、 Belanger, Patrice C.,Williams, Haydn W. R.. "Syntheses of optically active 2-tetrahydrofuran derivatives". . p. 1383 - 1386. Retrieved 2007/10/02.