(R)-Diethyl 2-hydroxysuccinate

Base Information

• Chemical Name: (R)-Diethyl 2-hydroxysuccinate
• CAS No.: 7554-28-1
• Molecular Formula: C8H14O5
• Molecular Weight: 190.196
• Hs Code.: 2918199090
• European Community (EC) Number: 879-128-1
• DSSTox Substance ID: DTXSID90226474
• Nikkaji Number: J74.449B
• Wikidata: Q72488109
• Mol file: 7554-28-1.mol

Synonyms:7554-28-1;(R)-Diethyl 2-hydroxysuccinate;D-(+)-Malic Acid Diethyl Ester;Diethyl D-(+)-Malate;diethyl (2R)-2-hydroxybutanedioate;Butanedioic acid, hydroxy-, diethyl ester, (R)-;AI3-01727;Butanedioic acid, hydroxy-, diethyl ester, (2R)-;(r)-diethyl malate;Diethyl (+)-Malate;D-Malic Acid Diethyl Ester;SCHEMBL4388130;C8H14O5;DTXSID90226474;D-(+)-Apple Acid Diethyl Ester;MFCD02093483;AKOS022185975;CS-W015897;DS-6572;M1351;D81853;1,4-DIETHYL (2R)-2-HYDROXYBUTANEDIOATE;EN300-7422260;A865665

Chemical Property of (R)-Diethyl 2-hydroxysuccinate

Chemical Property:

• Vapor Pressure: 0.000417mmHg at 25°C
• Refractive Index: 1.446
• Boiling Point: 281.6 °C at 760 mmHg
• PKA: 12.35±0.20(Predicted)
• Flash Point: 85 °C
• PSA: 72.83000
• Density: 1.149 g/cm³
• LogP: -0.13640
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: Water
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 190.08412354
• Heavy Atom Count: 13
• Complexity: 177

Purity/Quality:

99.0% ^*data from raw suppliers

Diethyl D-(+)-Malate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)CC(C(=O)OCC)O
• Isomeric SMILES: CCOC(=O)C[C@H](C(=O)OCC)O
• Uses: Diethyl D-Malate (cas# 7554-28-1) is a compound useful in organic synthesis.

Technology Process of (R)-Diethyl 2-hydroxysuccinate

There total 20 articles about (R)-Diethyl 2-hydroxysuccinate 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: 99.0%

(2R,3R)-diethyl 2-(3,5-bis(trifluoromethyl)benzoyloxy)-3-hydroxysuccinate → diethyl (R)-malate (7554-28-1)

Guidance literature:

With (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(2-phenylpyridine(-1H))-iridium(III) hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In water; acetonitrile; at 40 ℃; for 1h; Sealed tube; Schlenk technique; Inert atmosphere; Irradiation;

DOI:10.3762/bjoc.10.223

Reference yield: 97.0%

ethanol (64-17-5) + D-Malic acid (636-61-3,78644-42-5) → diethyl (R)-malate (7554-28-1)

Guidance literature:

With thionyl chloride;

DOI:10.1021/jo9910987

Reference yield: 96.0%

cyclic thionocarbonate of diethyl (R,R)-tartrate → diethyl (R)-malate (7554-28-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); diphenylsilane; In benzene; for 1h; Heating;

DOI:10.1081/SCC-120015803

upstream raw materials:

ethanol

D-Malic acid

L-aspartic acid diethyl ester

(2R)-2-Benzoyloxy-bernsteinsaeuredimethylester

Downstream raw materials:

diethyl (2R,3S)-3-(2-benzyloxyethyl)malate

(+)-(R)-ethyl 4-benzyloxy-3-hydroxybutanoate

(R)-1,2,4-butanetriol

(R)-4-ethoxy-2-hydroxy-4-oxobutanoic acid

Refernces

• 1、 Sunnapu, Ranganayakulu,Rajendar, Goreti. "A Concise Stereoselective Total Synthesis of Methoxyl Citreochlorols and Their Structural Revisions". . p. 1637 - 1642. Retrieved 2021/03/15.
• 2、 Imaizumi, Ryoya,Ogawa, Narihito. "Stereoselective Synthesis of Coreoside D and Determination of Its Absolute Configuration". supporting information. p. 1409 - 1412. Retrieved 2020/11/23.