Pentanedioic acid, 2-hydroxy-, dimethyl ester, (2S)-

Base Information

• Chemical Name: Pentanedioic acid, 2-hydroxy-, dimethyl ester, (2S)-
• CAS No.: 55094-97-8
• Molecular Formula: C7H12O5
• Molecular Weight: 176.169
• DSSTox Substance ID: DTXSID90450818
• Nikkaji Number: J1.161.617H
• Wikidata: Q82270640
• Mol file: 55094-97-8.mol

Synonyms:55094-97-8;(S)-Dimethyl 2-hydroxypentanedioate;Pentanedioic acid, 2-hydroxy-, dimethyl ester, (2S)-;Dimethyl (2S)-2-hydroxypentanedioate;Dimethyl (S)-2-hydroxypentanedioate;1,5-dimethyl (2S)-2-hydroxypentanedioate;SCHEMBL14436811;DTXSID90450818;(S)-Dimethyl2-hydroxypentanedioate;MFCD27925326;(S)-2-Hydroxyglutaric acid dimethyl ester;W17109;EN300-1174672

Chemical Property of Pentanedioic acid, 2-hydroxy-, dimethyl ester, (2S)-

Chemical Property:

• PSA: 72.83000
• LogP: -0.52650
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 176.06847348
• Heavy Atom Count: 12
• Complexity: 165

Purity/Quality:

99% ^*data from raw suppliers

Pentanedioicacid,2-hydroxy-,dimethylester,(2S)- ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)CCC(C(=O)OC)O
• Isomeric SMILES: COC(=O)CC[C@@H](C(=O)OC)O

Technology Process of Pentanedioic acid, 2-hydroxy-, dimethyl ester, (2S)-

There total 14 articles about Pentanedioic acid, 2-hydroxy-, dimethyl ester, (2S)- 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: 100.0%

methanol (67-56-1) + (S)-α-butyrolactone-α-carboxylic acid (21461-84-7) → (S)-dimethyl 2-hydroxypentanedioate (55094-97-8)

Guidance literature:

With hydrogenchloride; Heating;

DOI:10.1021/jo00001a076

Reference yield: 97.0%

methanol (67-56-1) + (2S)-tetrahydro-5-oxofuran-2-carboxylic acid (21461-84-7) → (S)-dimethyl 2-hydroxypentanedioate (55094-97-8)

Guidance literature:

With hydrogenchloride; In water; Inert atmosphere; Reflux;

DOI:10.1021/ol400484u

Reference yield: 76.0%

(S)-1-(2,5-dimethoxyphenoxy)-5-methoxy-1,5-dioxopentan-2-yl benzoate + sodium methylate (124-41-4) → (S)-dimethyl 2-hydroxypentanedioate (55094-97-8)

Guidance literature:

In methanol; at 0 - 20 ℃; for 18h;

DOI:10.1016/j.tetlet.2007.11.071

upstream raw materials:

diazomethane

L-hydroxyglutaric acid

methanol

L-glutamic acid

Downstream raw materials:

(S)-1,2,5-triacetoxy-pentane

dimethyl (S)-(-)-2-tosylglutarate

(2S)-1,2-di-O-p-methoxybenzylidene-1,2,5-pentanetriol

3-[(S)-2-(4-Methoxy-phenyl)-[1,3]dioxolan-4-yl]-propionaldehyde

Refernces

• 1、 -. "GADOLINIUM BEARING PCTA-BASED CONTRAST AGENTS". Page/Page column 33. . Retrieved 2020/03/02.
• 2、 Riatto, Valéria B.,Victor, Mauricio M.,Sousa, Jaqueline F.,Menegola, Carla. "Biotechnological properties of sponges from northeast Brazil: Cliona varians as a Biocatalyst for Enantioselective Reduction of Carbonyl Compounds". . p. 149 - 157. Retrieved 2018/12/13.