diethyl (2S,3S)-oxirane-2,3-dicarboxylate

Base Information

• Chemical Name: diethyl (2S,3S)-oxirane-2,3-dicarboxylate
• CAS No.: 73890-18-3
• Molecular Formula: C₈H₁₂O₅
• Molecular Weight: 188.18
• Hs Code.: 29189990
• DSSTox Substance ID: DTXSID70427326
• Nikkaji Number: J336.029F
• Wikidata: Q82239994
• ChEMBL ID: CHEMBL88967
• Mol file: 73890-18-3.mol

Synonyms:73890-18-3;diethyl (2S,3S)-oxirane-2,3-dicarboxylate;(2S,3S)-diethyl oxirane-2,3-dicarboxylate;DIETHYL (2S,3S)-(+)-2,3-EPOXYSUCCINATE;2,3-Oxiranedicarboxylicacid, 2,3-diethyl ester, (2S,3S)-;CHEMBL88967;SCHEMBL2387688;DTXSID70427326;LDFQMMUIJQDSAB-WDSKDSINSA-N;AKOS015919450;AT30759;Diethyl(2S,3S)-(+)-2,3-epoxysuccinate;(2S,3S)-epoxybutanedioic acid diethyl ester;CS-0169439;(2S,3S)-2,3-epoxybutanedioic acid diethyl ester;A837951;(2S,3S)-2,3-Oxiranedicarboxylic acid,diethyl ester;(2S)-Oxirane-2alpha,3beta-dicarboxylic acid diethyl ester

Chemical Property of diethyl (2S,3S)-oxirane-2,3-dicarboxylate

Chemical Property:

• Vapor Pressure: 0.0549mmHg at 25°C
• Refractive Index: 1.437-1.439
• Boiling Point: 233.7°C at 760 mmHg
• Flash Point: 95.5°C
• PSA: 65.13000
• Density: 1.233g/cm³
• LogP: -0.12000
• XLogP3: 0.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 188.06847348
• Heavy Atom Count: 13
• Complexity: 191

Purity/Quality:

99% ^*data from raw suppliers

DIETHYL (2S,3S)-(+)-2,3-EPOXYSUCCINATE 95.00% ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 37/39-26

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of diethyl (2S,3S)-oxirane-2,3-dicarboxylate

There total 17 articles about diethyl (2S,3S)-oxirane-2,3-dicarboxylate 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: 90.0%

diethyl (2S,3R)-(+)-erythro-2-hydroxy-3-bromosuccinate (80640-15-9) → (2S,3S)-diethyl oxirane-2,3-dicarboxylate (3291-46-1,3291-47-2,61937-48-2,66647-17-4,74243-85-9,73890-18-3)

Guidance literature:

With sodium ethanolate; In ethanol; at 20 ℃;

DOI:10.1021/jo050664x

Reference yield: 88.0%

ethanol (64-17-5) + (+)-(2S,3S)-trans-Oxiran-2,3-dicarbonsaeure-L-Arginin-Salz (93713-32-7) → (2S,3S)-diethyl oxirane-2,3-dicarboxylate (3291-46-1,3291-47-2,61937-48-2,66647-17-4,74243-85-9,73890-18-3)

Guidance literature:

With sulfuric acid; for 4.5h; Heating;

DOI:10.1002/hlca.200390015

Reference yield: 84.0%

diethyl (2RS,3SR)-2-hydroxy-3-(4-methylphenylsulfonyloxy)butane-1,4-dioate → (2SR,3SR)-oxirane-2,3-dicarboxylic acid diethyl ester (3291-46-1,3291-47-2,61937-48-2,66647-17-4,73890-18-3,74243-85-9)

Guidance literature:

With sodium ethanolate; In ethanol; at 0 ℃; for 1h;

upstream raw materials:

2-Bromo-3-hydroxy-succinic acid diethyl ester

diethyl Fumarate

but-2-enedioic acid diethyl ester

ethanol

Downstream raw materials:

trans-2,3-bis(ethoxycarbonyl)oxirane

diethylmalate

(2S,3S)-ethyl-3-((S)-1-oxo-1-((1-(4-sulfamoylphenyl)-1H-1,2,3-triazol-4-yl)methylamino)-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

(2S,3S)-ethyl-3-((S)-1-((1-(3,5-bis(trifluoromethyl)phenyl)-1H-1,2,3-triazol-4-yl)methylamino)-1-oxo-3-(thiazol-4-yl)propan-2-ylcarbamoyl)oxirane-2-carboxylate

Refernces

• 1、 -. "2,3-EPOXY SUCCINYL DERIVATIVE, PREPARATION METHOD THEREFOR, AND USES THEREOF". Paragraph 0220; 0221; 0222. . Retrieved 2019/01/17.
• 2、 Shi, Ming W.,Stewart, Scott G.,Sobolev, Alexandre N.,Dittrich, Birger,Schirmeister, Tanja,Luger, Peter,Hesse, Malte,Chen, Yu-Sheng,Spackman, Peter R.,Spackman, Mark A.,Grabowsky, Simon. "Approaching an experimental electron density model of the biologically active trans-epoxysuccinyl amide group—Substituent effects vs. crystal packing". supporting information. . Retrieved 2017/10/17.