Ethyl (2R,3R)-2,3-epoxybutyrate

Base Information

• Chemical Name: Ethyl (2R,3R)-2,3-epoxybutyrate
• CAS No.: 118712-09-7
• Molecular Formula: C6H10 O3
• Molecular Weight: 130.14
• European Community (EC) Number: 243-300-9
• DSSTox Substance ID: DTXSID90922762
• Mol file: 118712-09-7.mol

Synonyms:Ethyl (2R,3R)-2,3-epoxybutyrate;118712-09-7;19780-35-9;ethyl (2R,3R)-3-methyloxirane-2-carboxylate;ETHYL (2R,3R)-2,3-EPOXY-3-METHYLPROPANOATE, 96;ethyl 3-methyloxirane-2-carboxylate;Oxiranecarboxylic acid, 3-methyl-, ethyl ester;DTXSID90922762;AKOS006237183;Ethyl (2R,3R)-2,3-epoxy-3-methylpropanoate;Ethyl(2R,3R)-2,3-epoxy-3-methylpropanoate,96;J-640387;J-640428;J-800393;J-800414

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

Chemical Property:

• Vapor Pressure: 6.86mmHg at 25°C
• Boiling Point: 172-174°C/760mmHg
• Flash Point: 45.4°C
• PSA: 38.83000
• Density: 1.099g/cm³
• LogP: 0.33680
• Storage Temp.: Flammables area
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 130.062994177
• Heavy Atom Count: 9
• Complexity: 122

Purity/Quality:

98%min ^*data from raw suppliers

ETHYL-(2R,3R)-2,3-EPOXY-3-METHYLPROPANOATE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1C(O1)C
• Isomeric SMILES: CCOC(=O)[C@H]1[C@H](O1)C

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

There total 9 articles about Ethyl (2R,3R)-2,3-epoxybutyrate 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: 91.0%

ethyl 2-<(p-nitrobenzenesulfonyl)oxy>-3-hydroxybutanoate (136805-79-3,136805-84-0) → ethyl cis-3-methyl-1-oxirane-2-carboxylate (19780-35-9,25834-24-6,36099-48-6,38053-37-1,58917-48-9,82769-14-0,110508-08-2,118712-09-7,136889-93-5)

Guidance literature:

With triethylamine; In acetonitrile; Heating;

DOI:10.1021/jo00024a013

Reference yield: 84.0%

(S)-2-Chloro-3-hydroxy-butyric acid ethyl ester (89490-41-5,110444-42-3,110444-43-4,121210-32-0,121210-33-1,134451-51-7,135266-67-0,150131-74-1,150282-90-9) → ethyl (2R,3S)- and (2S,3S)-2,3-epoxybutanoate (19780-35-9,25834-24-6,36099-48-6,38053-37-1,58917-48-9,82769-14-0,110508-08-2,118712-09-7,136889-93-5)

Guidance literature:

With sodium ethanolate; In ethanol;

DOI:10.1016/S0040-4039(00)85221-1

Reference yield:

ethyl 2-chloro-3-oxo-butyrate (609-15-4) → ethyl (2R,3S)- and (2S,3S)-2,3-epoxybutanoate (19780-35-9,25834-24-6,36099-48-6,38053-37-1,58917-48-9,82769-14-0,110508-08-2,118712-09-7,136889-93-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 68 percent / H₂O / 24 h / 30 °C / Saccharomyces cerevisiae, sucrose

2: 65 percent / NaOEt / ethanol / 0.5 h / 0 °C

With sodium ethanolate; In ethanol; water;

DOI:10.1055/s-1993-25895

upstream raw materials:

(S)-2-Chloro-3-hydroxy-butyric acid ethyl ester

ethyl 2-chloro-3-oxo-butyrate

ethyl 2-<(p-nitrobenzenesulfonyl)oxy>-3-hydroxybutanoate

ethyl 2-<(p-nitrobenzenesulfonyl)oxy>-3-hydroxybutanoate

Downstream raw materials:

ethyl (2S,3R)-2-(4-chlorophenoxy)-3-hydroxybutanoate

(2R,3S)-3-Benzyloxy-2-methoxymethoxy-butyric acid ethyl ester

ethyl (2R,3S)-3-benzyloxy-2-hydroxybutanoate

Refernces

• 1、 Akita,Todoroki,Endo,Ikari,Oishi. "Practical synthesis of optically pure methyl (2R,3S)-2,3-epoxybutanoate via microbial asymmetric reduction of α-chloroacetoacetate". . p. 513 - 516. Retrieved 2007/10/02.
• 2、 Petit, Yves,Sanner, Caroline,Larcheveque, Marc. "A Convenient Synthesis of Enantiomerically Pure (2R,3S)- and (2S,3R)-3-Hydroxy-2-methylbutanoic Esters". . p. 538 - 540. Retrieved 2007/10/02.