(S)-2-Hydroxysuccinic Acid Methyl Ester

Base Information

• Chemical Name: (S)-2-Hydroxysuccinic Acid Methyl Ester
• CAS No.: 66212-45-1
• Molecular Formula: C5H8O5
• Molecular Weight: 148.116
• DSSTox Substance ID: DTXSID80566614
• Nikkaji Number: J2.230.225F
• Wikidata: Q82452303
• Mol file: 66212-45-1.mol

Synonyms:66212-45-1;(S)-2-Hydroxysuccinic Acid Methyl Ester;(S)-3-Hydroxy-4-methoxy-4-oxobutanoic acid;(3S)-3-Hydroxy-4-methoxy-4-oxobutanoic acid;L-malic acid monomethyl ester;SCHEMBL222024;DTXSID80566614;AKOS006377434;(S)-3-Hydroxy-4-methoxy-4-oxobutanoicacid;CS-0454702

Chemical Property of (S)-2-Hydroxysuccinic Acid Methyl Ester

Chemical Property:

• Vapor Pressure: 3.08E-05mmHg at 25°C
• Melting Point: 70-72°C
• Boiling Point: 318.0±32.0 °C(Predicted)
• PKA: 4.03±0.19(Predicted)
• PSA: 83.83000
• Density: 1.383±0.06 g/cm3(Predicted)
• LogP: -1.00500
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: DMSO (Slightly), Methanol (Sparingly)
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 148.03717335
• Heavy Atom Count: 10
• Complexity: 141

Purity/Quality:

99% ^*data from raw suppliers

(S)-2-HydroxysuccinicAcidMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC(=O)O)O
• Isomeric SMILES: COC(=O)[C@H](CC(=O)O)O
• Uses: (S)-2-Hydroxysuccinic Acid Methyl Ester (cas# 66212-45-1) is a compound useful in organic synthesis.

Technology Process of (S)-2-Hydroxysuccinic Acid Methyl Ester

There total 8 articles about (S)-2-Hydroxysuccinic Acid Methyl Ester 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: 98.0%

methanol (67-56-1) + (S)-Malic acid (97-67-6,78644-42-5) → (2S)-2-hydroxy-butanedioic acid 1-mono methyl ester (66212-45-1)

Guidance literature:

(S)-Malic acid; With trifluoroacetic anhydride; for 1.5h; Inert atmosphere;

methanol; for 2h; regioselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2019.06.050

Reference yield: 87.0%

methanol (67-56-1) + (3S)-2,5-dioxotetrahydrofuran-3-yl trifluoroacetate (99529-36-9) → (2S)-2-hydroxy-butanedioic acid 1-mono methyl ester (66212-45-1)

Guidance literature:

Ambient temperature;

DOI:10.1016/S0957-4166(00)80433-4

Reference yield: 56.8%

tetramethylorthosilicate (681-84-5) + (S)-Malic acid (97-67-6,78644-42-5) → (2S)-2-hydroxy-butanedioic acid 1-mono methyl ester (66212-45-1)

Guidance literature:

With methanol; at 15 - 20 ℃; for 30h; regioselective reaction;

DOI:10.1039/b814488e

upstream raw materials:

methanol

(S)-Malic acid

(S)-3-Hydroxy-dihydro-furan-2,5-dione

(3S)-2,5-dioxotetrahydrofuran-3-yl trifluoroacetate

Downstream raw materials:

methyl (5S)-2-oxo-1,3-oxazolidine-5-carboxylate

(S)-1,2,4-butanetriol

methyl (2S)-4-[(tert-butyldimethylsilyl)oxy]-2-hydroxybutanoate

methyl (5R)-2-oxo-1,3-oxazolidine-5-carboxylate

Refernces

• 1、 Cammas, Sandrine,Renard, Isabelle,Boutault, Karine,Guerin, Philippe. "A NOVEL SYNTHESIS OF OPTICALLY ACTIVE 4-BENZYLOXY- AND 4-ALKYOXYCARBONYL-2-OXETANONES". . p. 1925 - 1930. Retrieved 1993.
• 2、 -. "A S - (+) -3 - hydroxy tetrahydrofuran chemical synthesis method". Paragraph 0017-0019. . Retrieved 2019/04/04.
• 3、 -. "POSITIVE ALLOSTERIC MODULATORS OF MUSCARINIC M2 RECEPTOR". Paragraph 1054-1056. . Retrieved 2018/11/21.