(R)-methyl oxirane-2-carboxylate

Base Information

• Chemical Name: (R)-methyl oxirane-2-carboxylate
• CAS No.: 111058-32-3
• Molecular Formula: C₄H₆O₃
• Molecular Weight: 102.09
• Hs Code.: 2918990090
• European Community (EC) Number: 601-036-5
• DSSTox Substance ID: DTXSID60432146
• Nikkaji Number: J623.384H
• Wikidata: Q72486417
• Mol file: 111058-32-3.mol

Synonyms:111058-32-3;(R)-Methyglycidate;(R)-methyl oxirane-2-carboxylate;methyl (2R)-oxirane-2-carboxylate;Methyl (2R)-glycidate;methyl (R)-glycidate;(R)-methylglycidate;(r)-methyl glycidate;Oxiranecarboxylic acid, methyl ester, (2R)-;Methyl (R)-oxiranecarboxylate;MFCD00274191;(R)-Glycidic Acid Methyl Ester;methyl (R)-oxirane-2-carboxylate;methyl(R)-glycidate;methyl-(R)-glycidate;Methyl(2R)-glycidate;Methyl(2R)-oxirane-2-carboxylate;SCHEMBL840388;DTXSID60432146;methyl(2R)-oxiran-2-carboxylate;methyl (2R)-2-oxiranecarboxylate;YKNYRRVISWJDSR-GSVOUGTGSA-N;methyl (2R)-2,3-epoxypropanoate;methyl (2R)-oxiran-2-carboxylate;AMY31968;BCP16542;CS-B1238;AKOS015899909;(R)-Oxiranecarboxylic acid methyl ester;AS-15863;H11420;J-002513;Methyl (2R)-glycidate, optical purity ee: 94% (GLC), 97%

Chemical Property of (R)-methyl oxirane-2-carboxylate

Chemical Property:

• Appearance/Colour: Clear colorless or slightly yellow liquid
• Vapor Pressure: 41.693mmHg at 25°C
• Refractive Index: n20/D 1.42(lit.)
• Boiling Point: 97.45 °C at 760 mmHg
• Flash Point: 26.199 °C
• PSA: 38.83000
• Density: 1.247 g/cm³
• LogP: -0.44180
• Storage Temp.: 2-8°C
• Solubility.: Acetonitrile (Slightly), Chloroform (Soluble), Ethyl Acetate (Slightly)
• XLogP3: -0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 102.031694049
• Heavy Atom Count: 7
• Complexity: 88.9

Purity/Quality:

99% ^*data from raw suppliers

(R)-GlycidicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CO1
• Isomeric SMILES: COC(=O)[C@H]1CO1
• Uses: (R)-Methyglycidate is used in the preparation of antibacterial oxazolidinones.

Technology Process of (R)-methyl oxirane-2-carboxylate

There total 14 articles about (R)-methyl oxirane-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: 82.0%

R-oxiranecarboxylic acid potassium salt (82044-23-3) + dimethyl sulfate (77-78-1) → methyl (2R)-glycidate (4538-50-5,85485-00-3,118712-39-3,111058-32-3)

Guidance literature:

With 18-crown-6 ether; In acetonitrile; for 1h;

Reference yield: 65.0%

potassium de l'acide (S)-(-)-epoxy-2,3 propionique (82079-45-6) + dimethyl sulfate (77-78-1) → methyl (2S)-glycidate (4538-50-5,85485-00-3,111058-32-3,118712-39-3)

Guidance literature:

With 18-crown-6 ether; In acetonitrile;

DOI:10.1016/S0040-4039(00)96028-3

Reference yield: 44.0%

methyl glycidate (4538-50-5) → methyl (2R)-2,3-dihydroxypropanoate (18289-89-9,15909-76-9) + methyl (2S)-glycidate (4538-50-5,85485-00-3,111058-32-3,118712-39-3)

Guidance literature:

With water; In neat (no solvent); at 23 ℃; Reagent/catalyst; enantioselective reaction; Sealed tube;

DOI:10.1016/j.tet.2014.03.043

upstream raw materials:

potassium de l'acide (S)-(-)-epoxy-2,3 propionique

dimethyl sulfate

methyl glycidate

R-oxiranecarboxylic acid potassium salt

Downstream raw materials:

(R)-methyl 3-(4-fluorophenyl)-2-hydroxypropanoate

methyl (2S)-2-hydroxy-3-{N-[4-(4-chlorophenoxy)phenyl],N-methanesulfonylamino}propionate

C₁₇H₁₇F₃N₂O₆S

C₂₃H₂₃NO₆S

Refernces

• 1、 White, David E.,Jacobsen, Eric N.. "New oligomeric catalyst for the hydrolytic kinetic resolution of terminal epoxides under solvent-free conditions". . p. 3633 - 3638. Retrieved 2003.
• 2、 Zheng, Yong,Song, Wei-Bin,Xuan, Li-Jiang. "The asymmetric total synthesis of (+)-salvianolic acid A". supporting information. p. 5047 - 5050. Retrieved 2016/07/25.