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

Base Information

• Chemical Name: diethyl (2R,3R)-oxirane-2,3-dicarboxylate
• CAS No.: 74243-85-9
• Molecular Formula: C8H12O5
• Molecular Weight: 188.18
• European Community (EC) Number: 623-290-6
• DSSTox Substance ID: DTXSID80369960
• Nikkaji Number: J336.030J
• Wikidata: Q72461905
• ChEMBL ID: CHEMBL89322
• Mol file: 74243-85-9.mol

Synonyms:74243-85-9;diethyl (2R,3R)-oxirane-2,3-dicarboxylate;(2R,3R)-Diethyl 2,3-epoxysuccinate;MFCD00797924;(2R,3R)-diethyl oxirane-2,3-dicarboxylate;CHEMBL89322;SCHEMBL2387697;diethyl (2R,3R)-epoxysuccinate;DTXSID80369960;LDFQMMUIJQDSAB-PHDIDXHHSA-N;MFCD18533536;AKOS017343325;Diethyl-(2R,3R)-2,3-epoxysuccinate;AT30758;diethyl (r,r)-oxirane-2,3-dicarboxylate;CS-0169440;CS-0169441;Diethyl-(2R,3R)-(-)-2,3-epoxysuccinate;(2R,3R)-Diethyl 2,3-epoxysuccinate, 96%;diethyl (2R,3R)-(-)-2,3-EPOXYSUCCINATE;rel-Diethyl (2R,3R)-oxirane-2,3-dicarboxylate;2,3-diethyl (2R,3R)-oxirane-2,3-dicarboxylate;A905118;DIETHYL(2R,3R)-(-)-2,3-EPOXYSUCCINATE;EN300-19632292;Z1255488127;(2R)-Oxirane-2beta,3alpha-dicarboxylic acid diethyl ester

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

Chemical Property:

• Vapor Pressure: 0.0549mmHg at 25°C
• Refractive Index: n20/D 1.4380(lit.)
• Boiling Point: 233.7 °C at 760 mmHg
• Flash Point: 95.5 °C
• PSA: 65.13000
• Density: 1.233 g/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:

97% ^*data from raw suppliers

(2R,3R)-Diethyl 2,3-epoxysuccinate 96% ^*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

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1C(O1)C(=O)OCC
• Isomeric SMILES: CCOC(=O)[C@H]1[C@@H](O1)C(=O)OCC
• Uses: (2R,3R)-Diethyl 2,3-epoxysuccinate may be used in the preparation of ethyl (2R,3S)-4-hydroxy-2,3-epoxybutyrate via reduction using sodium borohydride

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

There total 23 articles about diethyl (2R,3R)-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: 90.0%

diethyl (2R,3S)-(-)-erythro-2-hydroxy-3-bromosuccinate (80640-14-8) → trans-2,3-bis(ethoxycarbonyl)oxirane (74243-85-9)

Guidance literature:

With sodium ethanolate; In ethanol; at 0 - 10 ℃; for 2.33333h; Inert atmosphere;

DOI:10.15227/orgsyn.073.0184

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

upstream raw materials:

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

diethyl Fumarate

but-2-enedioic acid diethyl ester

ethanol

Downstream raw materials:

diethylmalate

ethyl (2S,3S)-3-carboxylate oxirane-2-carboxylic acid

2-ethyl 3-(4-nitrophenyl) (2S,3S)-oxirane-2,3-dicarboxylate

(-)-trans-2,3-oxiranedicarboxylic acid