(S)-Dimethyl 2-hydroxysuccinate

Base Information

• Chemical Name: (S)-Dimethyl 2-hydroxysuccinate
• CAS No.: 617-55-0
• Deprecated CAS: 113240-52-1
• Molecular Formula: C6H10O5
• Molecular Weight: 162.142
• Hs Code.: 29181990
• European Community (EC) Number: 432-310-0,629-292-3
• DSSTox Substance ID: DTXSID50892497
• Nikkaji Number: J96.546D
• Wikidata: Q72470819
• Mol file: 617-55-0.mol

Synonyms:617-55-0;(S)-Dimethyl 2-hydroxysuccinate;Dimethyl L-malate;Dimethyl (S)-(-)-malate;L-(-)-Malic Acid Dimethyl Ester;Dimethyl (2S)-2-hydroxybutanedioate;(-)-dimethyl malate;Butanedioic acid, hydroxy-, dimethyl ester, (2S)-;EC 432-310-0;1,4-dimethyl (2S)-2-hydroxybutanedioate;dimethyl-l-malate;L-(-)-Apple Acid Dimethyl Ester;di-methyl (s)-malate;Dimethyl L-(-)-Malate;(s)-(-)-dimethyl malate;Dimethyl (S)-(-) malate;(S)-Dimethyl2-hydroxysuccinate;SCHEMBL1823637;Dimethyl (S)-2-hydroxysuccinate;L-(-)-Malic acid dimethylester;DTXSID50892497;YSEKNCXYRGKTBJ-BYPYZUCNSA-N;Dimethyl (2S)-2-hydroxysuccinate;Dimethyl (S)-(-)-malate, 98%;MFCD00066215;3-AMINO-4-M-TOLYLBUTANOICACID;AKOS015850984;CS-W007994;CS-17326;M1343;EN300-198444;O10223;J-520343

Chemical Property of (S)-Dimethyl 2-hydroxysuccinate

Chemical Property:

• Appearance/Colour: Colorless transparent liquid
• Vapor Pressure: 0.004mmHg at 25°C
• Refractive Index: n20/D 1.441
• Boiling Point: 249.629 °C at 760 mmHg
• PKA: 11.72±0.20(Predicted)
• Flash Point: 100.054 °C
• PSA: 72.83000
• Density: 1.224 g/cm³
• LogP: -0.91660
• Storage Temp.: 2-8°C
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 162.05282342
• Heavy Atom Count: 11
• Complexity: 153

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl (S)-(?)-malate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38-43-41-10
• Safety Statements: 26-36-43-37/39-24

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CC(C(=O)OC)O
• Isomeric SMILES: COC(=O)C[C@@H](C(=O)OC)O
• Uses: This chiral synthon has been used to prepare cytochrome P450 metabolites of arachidonic acid, and cyclic sulfolanes with HIV-1 protease inhibition potential.

Technology Process of (S)-Dimethyl 2-hydroxysuccinate

There total 8 articles about (S)-Dimethyl 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:

Dimethyl 2-oxosuccinate (25007-54-9) → dimethyl (S)-malate (617-55-0) + (R)-dimethyl malate (70681-41-3)

Guidance literature:

With Ru((R)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)(MeCN)(1,3:5,6-η-C8H11)(BF4); hydrogen; In acetone; at 50 ℃; for 28h; under 76000 Torr; Yield given; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1139/v98-189

Reference yield:

malic acid dimethyl ester (38115-87-6) → malic acid monomethyl ester (66178-02-7) + dimethyl (S)-malate (617-55-0) + (R)-dimethyl malate (70681-41-3)

Guidance literature:

With sodium hydroxide; potassium dihydrogenphosphate; In methanol; water; at 0 ℃; for 7h; Yields of byproduct given;

Reference yield:

Dimethyl (R,S)-2-O-Acetylmalate (92381-33-4) → dimethyl (S)-malate (617-55-0) + Dimethyl (S)-(-)-2-O-Acetylmalate (85828-07-5) + (R)-dimethyl malate (70681-41-3) + (R)-2-Acetoxy-bernsteinsaeuredimethylester (72229-29-9)

Guidance literature:

With sodium hydroxide; potassium dihydrogenphosphate; In methanol; water; at 0 ℃; for 7h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

upstream raw materials:

Dimethyl 2-oxosuccinate

malic acid dimethyl ester

Dimethyl (R,S)-2-O-Acetylmalate

tetramethylorthosilicate

Downstream raw materials:

(S)-2-(3-Phenyl-2-propenoyl)-oxybutan-1,4-dicarbonsaeuredimethylester

(R)-2-Benzyloxyamino-succinic acid dimethyl ester

dimethyl (S)-2-(benzyloxyamino)butane-1,4-dioate

dimethyl (-)-menthoxycarbonyl-S-malate

Refernces

• 1、 Ansell, Richard J.,Meegan, Jonathan E.,Barrett, Simon A.,Warrinner, Stuart L.. "On the interactions of alkyl 2-hydroxycarboxylic acids with alkoxysilanes 2. Complexation and esterification of di- and tricarboxylic acids". scheme or table. p. 1460 - 1470. Retrieved 2009/06/05.
• 2、 Daley, Christopher J.A.,Wiles, Jason A.,Bergens, Steven H.. "Application of [Ru((R)-BINAP)(MeCN)(1-3:5,6-η-C8H11)](BF4) as a catalyst precursor for enantioselective hydrogenations". . p. 1447 - 1456. Retrieved 2007/10/03.