Ethyl (2R)-2,3-epoxypropanoate

Base Information

• Chemical Name: Ethyl (2R)-2,3-epoxypropanoate
• CAS No.: 111058-33-4
• Molecular Formula: C₅H₈O₃
• Molecular Weight: 116.117
• Hs Code.: 29189990
• European Community (EC) Number: 866-955-8
• DSSTox Substance ID: DTXSID80363761
• Nikkaji Number: J623.386D
• Wikidata: Q72474760
• Mol file: 111058-33-4.mol

Synonyms:111058-33-4;ETHYL (2R)-2,3-EPOXYPROPANOATE;(R)-ethyl oxirane-2-carboxylate;ethyl (2R)-oxirane-2-carboxylate;ETHYL(2R)-2,3-EPOXYPROPANOATE;ethyl (R)-oxirane-2-carboxylate;2-Oxiranecarboxylicacid, ethyl ester, (2R)-;ethyl 2(R)-epoxypropanoate;SCHEMBL3039889;(R)-ethyloxirane-2-carboxylate;DTXSID80363761;Ethyl-(2R)-2,3-epoxypropionate;ethyl-(2r)-2,3-epoxyproprionate;AMY31967;MFCD00062872;AKOS015909017;AS-30251;oxirane-2(R)-carboxylic acid ethyl ester;(2R)-2,3-Epoxypropanoic acid ethyl ester;CS-0129136;EN300-6981189;Z1255372614

Chemical Property of Ethyl (2R)-2,3-epoxypropanoate

Chemical Property:

• Appearance/Colour: clear colorless to pink or yellowish liquid
• Vapor Pressure: 13.5mmHg at 25°C
• Refractive Index: 1.419-1.421
• Boiling Point: 123.1 °C at 760 mmHg
• Flash Point: 38.3 °C
• PSA: 38.83000
• Density: 1.18 g/cm³
• LogP: -0.05170
• Storage Temp.: Refrigerator (+4°C)
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 116.047344113
• Heavy Atom Count: 8
• Complexity: 99.8

Purity/Quality:

99% ^*data from raw suppliers

Ethyl(R)-(+)-Glycidate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-10
• Safety Statements: 16

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1CO1
• Isomeric SMILES: CCOC(=O)[C@H]1CO1
• Uses: Ethyl (R)-(+)-Glycidate is used in the synthesis of potent inhibitors of a Shikimate pathway enzyme from Mycobacterium tuberculosis. It is also used to prepare acaterin, a naturally occurring ACAT inhibitor.

Technology Process of Ethyl (2R)-2,3-epoxypropanoate

There total 8 articles about Ethyl (2R)-2,3-epoxypropanoate 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: 85.0%

diethyl sulfate (64-67-5) + R-oxiranecarboxylic acid potassium salt (82044-23-3) → ethyl (R)-(+)-2,3-epoxypropanoate (4660-80-4,93264-11-0,111058-34-5,111058-33-4)

Guidance literature:

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

Reference yield: 81.0%

ethyl bromide (74-96-4) + R-oxiranecarboxylic acid potassium salt (82044-23-3) → ethyl (R)-(+)-2,3-epoxypropanoate (4660-80-4,93264-11-0,111058-34-5,111058-33-4)

Guidance literature:

With N-benzyl-N,N,N-triethylammonium chloride; In dichloromethane; for 16h; Reflux;

DOI:10.15227/orgsyn.075.0037

Reference yield: 65.0%

R-oxiranecarboxylic acid potassium salt (82044-23-3) + ethyl iodide (75-03-6) → ethyl (R)-(+)-2,3-epoxypropanoate (4660-80-4,93264-11-0,111058-34-5,111058-33-4)

Guidance literature:

With 18-crown-6 ether; In acetonitrile;

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

upstream raw materials:

diethyl sulfate

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

ethyl iodide

D-Serine

Downstream raw materials:

C₁₆H₂₄O₄

C₃₇H₄₄O₁₀P₂

C₃₇H₄₄O₁₀P₂

(1R,2R)-2-(3,4-difluorophenyl)-1-cyclopropanecarboxylic acid ethyl ester

Refernces

• 1、 Krecmerova, Marcela,Budesinsky, Milos,Masojidkova, Milena,Holy, Antonin. "Synthesis of optically active N6-alkyl derivatives of (R)-3-(adenin-9-yl)-2-hydroxypropanoic acid and related compounds". . p. 931 - 950. Retrieved 2003.
• 2、 Reichau, Sebastian,Jiao, Wanting,Walker, Scott R.,Hutton, Richard D.,Baker, Edward N.,Parker, Emily J.. "Potent inhibitors of a shikimate pathway enzyme from Mycobacterium tuberculosis: Combining mechanism- and modeling-based design". scheme or table. p. 16197 - 16207. Retrieved 2012/03/26.