Dimethyl (S)-(+)-2-Methylglutarate

Base Information

• Chemical Name: Dimethyl (S)-(+)-2-Methylglutarate
• CAS No.: 10171-92-3
• Molecular Formula: C8H14O4
• Molecular Weight: 174.197
• Hs Code.: 2917190090
• DSSTox Substance ID: DTXSID80453378
• Nikkaji Number: J72.007K
• Wikidata: Q82274504
• Mol file: 10171-92-3.mol

Synonyms:10171-92-3;Dimethyl (S)-(+)-2-Methylglutarate;(S)-Dimethyl 2-methylpentanedioate;(S)-(+)-2-Methylglutaric Acid Dimethyl Ester;dimethyl (2S)-2-methylpentanedioate;DTXSID80453378;Pentanedioic acid, 2-methyl-, 1,5-dimethyl ester, (2S)-;(S)-Dimethyl2-methylpentanedioate;Dimethyl (S)-2-methylpentanedioate;MFCD00671564;AKOS015840170;(S)-2-Methylglutaric acid dimethyl ester;AS-69873;CS-0321547;M1230;T71529;1,5-DIMETHYL (2S)-2-METHYLPENTANEDIOATE;J-000485;Pentanedioic acid,2-methyl-,1,5-dimethyl ester,(2S)-

Chemical Property of Dimethyl (S)-(+)-2-Methylglutarate

Chemical Property:

• Vapor Pressure: 0.264mmHg at 25°C
• Refractive Index: 24.5 ° (C=neat)
• Boiling Point: 204.416 °C at 760 mmHg
• Flash Point: 90.802 °C
• PSA: 52.60000
• Density: 1.037 g/cm³
• LogP: 0.74870
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 174.08920892
• Heavy Atom Count: 12
• Complexity: 164

Purity/Quality:

98%,99%, ^*data from raw suppliers

Dimethyl (S)-(+)-2-Methylglutarate ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of Dimethyl (S)-(+)-2-Methylglutarate

There total 14 articles about Dimethyl (S)-(+)-2-Methylglutarate 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: 33.0%

methyl (4S)-(4-methoxy-2-methylphenyl)pentanoate (471261-18-4) + diazomethane (186581-53-3,908094-01-9,334-88-3) → (S)-(+)-dimethyl-2-methylglutarate (10171-92-3)

Guidance literature:

methyl (4S)-(4-methoxy-2-methylphenyl)pentanoate; With ruthenium trichloride; sodium periodate; In tetrachloromethane; acetonitrile; at 20 ℃; for 18h;

diazomethane; In diethyl ether;

DOI:10.1248/cpb.53.565

Reference yield: 33.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + methyl (4S)-(2-methoxy-4-methylphenyl)pentanoate (170423-72-0) → (S)-(+)-dimethyl-2-methylglutarate (10171-92-3) + (S)-3-Methyl-2-oxo-hexanedioic acid dimethyl ester

Guidance literature:

methyl (4S)-(2-methoxy-4-methylphenyl)pentanoate; With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 18h;

With hydrogenchloride; In water;

diazomethane; In diethyl ether;

DOI:10.1016/S0957-4166(01)00447-5

Reference yield: 22.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + methyl 4-(2'-methoxy-5'-methylphenyl)pentanoate (399535-04-7) → (S)-(+)-dimethyl-2-methylglutarate (10171-92-3) + (S)-3-Methyl-2-oxo-hexanedioic acid dimethyl ester

Guidance literature:

methyl 4-(2'-methoxy-5'-methylphenyl)pentanoate; With ruthenium trichloride; sodium periodate; In tetrachloromethane; water; acetonitrile; at 20 ℃; for 18h;

With hydrogenchloride; In water;

diazomethane; In diethyl ether;

DOI:10.1016/S0957-4166(01)00447-5

upstream raw materials:

methyl (+)-(Z)-2-carbomethoxycyclopropylidene acetate

methyl (-)-(E)-2-carbomethoxycyclopropylideneacetate

dimethyl 2-methylglutarate

diazomethane

Downstream raw materials:

(S)-2-methylglutaric acid

3-methyl-1-cyclopentene

1-methylcyclopent-1-ene

Refernces

• 1、 Ozaki, Eiji,Uragaki, Toshitaka,Sakashita, Keiichi,Sakimae, Akihiro. "Enzymatic Preparation of Alkanedicarboxylic Acid Monoesters". . p. 539 - 540. Retrieved 1995.
• 2、 Dydio, Pawel,Rubay, Christophe,Gadzikwa, Tendai,Lutz, Martin,Reek, Joost N. H.. ""Cofactor"-controlled enantioselective catalysis". supporting information; experimental part. p. 17176 - 17179. Retrieved 2011/12/13.
• 3、 Duan, Zheng-Chao,Hu, Xiang-Ping,Deng, Jun,Yu, Sai-Bo,Wang, Dao-Yong,Zheng, Zhuo. "Asymmetric synthesis of chiral glutaric acid derivatives via Rh-catalyzed enantioselective hydrogenation". experimental part. p. 588 - 592. Retrieved 2009/08/08.