Dimethyl d-tartrate

Base Information

• Chemical Name: Dimethyl d-tartrate
• CAS No.: 13171-64-7
• Molecular Formula: C6H10O6
• Molecular Weight: 178.142
• Hs Code.: 29181300
• European Community (EC) Number: 236-118-6
• Nikkaji Number: J135.635F
• Wikidata: Q106902858
• Mol file: 13171-64-7.mol

Synonyms:Dimethyl d-tartrate;13171-64-7;(-)-Dimethyl D-tartrate;Dimethyl D-(-)-Tartrate;Dimethyl-D-tartrate;dimethyl (2S,3S)-2,3-dihydroxybutanedioate;(2S,3S)-dimethyl 2,3-dihydroxysuccinate;dl-Dimethyl tartrate;DL-Dimethyl tartarate;meso-tartaric acid, dimethyl ester;Racemic dimethyl tartrate;Butanedioic acid, 2,3-dihydroxy-, dimethyl ester, (2S,3S)-;5057-96-5;608-69-5;Dimethyl (S(R*,R*))-tartrate;EINECS 236-118-6;Tartaric acid, dimethyl ester, DL-;Dimethyl [S(R*,R*)]-tartrate;Dimethyl (2S,3S)-2,3-Dihydroxysuccinate;dimethyl [2S,3S]-2,3-dihydroxybutanedioate;MFCD00008445;Tartaric acid, dimethyl ester, meso-;Dimetyl D-tartrate;D-(-)-Tartaric acid dimethyl ester;(2S,3S)-dimethyl tartrate;SCHEMBL590894;(-)-Dimethyl D-tartrate, 99%;AKOS024437565;AM81412;AS-11873;T1659;(−)-Dimethyl D-tartrate;D70237;dimethyl (2S,3S)-2,3-bis(oxidanyl)butanedioate;1,4-dimethyl (2S,3S)-2,3-dihydroxybutanedioate;A828184;J-006042;(2S,3S)-2,3-Dihydroxy-succinic acid dimethyl ester;(2S,3S)-2,3-dihydroxybutanedioic acid dimethyl ester;(-)-Dimethyl D-tartrate, purum, >=99.0% (sum of enantiomers, GC);Butanedioic acid, 2,3-dihydroxy-, 1,4-dimethyl ester, (2R,3R)-rel-

Chemical Property of Dimethyl d-tartrate

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 0.000467mmHg at 25°C
• Melting Point: 57-60 °C (dec.)(lit.)
• Refractive Index: -21 ° (C=1, H2O)
• Boiling Point: 280 °C at 760 mmHg
• PKA: 11.44±0.20(Predicted)
• Flash Point: 95.7 °C
• PSA: 93.06000
• Density: 1.367 g/cm³
• LogP: -1.94580
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: -1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 178.04773803
• Heavy Atom Count: 12
• Complexity: 157

Purity/Quality:

99% ^*data from raw suppliers

Dimethyl(2R,3R)-2,3-Dihydroxybutanedioate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 24/25-36/37-26

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

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

Technology Process of Dimethyl d-tartrate

There total 18 articles about Dimethyl d-tartrate 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) + D-tartaric acid (147-71-7,138508-61-9) → Dimethyl D-tartrate (13171-64-7)

Guidance literature:

With toluene-4-sulfonic acid; In toluene;

DOI:10.1002/chir.22814

Reference yield: 98.0%

methanol (67-56-1) + L-tartaric acid (87-69-4,133-37-9,147-71-7,147-73-9,526-83-0,138508-61-9) → dimethyl L-tartrate (608-68-4,608-69-5,5057-96-5,13171-64-7,117356-23-7)

Guidance literature:

With boric acid; at 20 ℃; for 18h;

DOI:10.1021/ol036123g

Reference yield: 97.0%

D-tartaric acid (147-71-7,138508-61-9) + trimethyl orthoformate (149-73-5) → Dimethyl D-tartrate (13171-64-7)

Guidance literature:

With Dowex 50W X₈ (H⁺ form); In methanol; at 50 ℃; for 22h; Inert atmosphere;

DOI:10.1007/s00706-013-1100-x

upstream raw materials:

methanol

D-tartaric acid

dimethylfumarate

trimethyl orthoformate

Downstream raw materials:

(2S,3S)-2-Hydroxy-3-((2S,3S,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-succinic acid dimethyl ester

(4S,5S)-2-(4-Benzoyloxymethyl-phenyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester

(4S,5S)-2-Ethyl-2-(4-methoxy-phenyl)-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester

(4S,5S)-2-Ethyl-2-phenyl-[1,3]dioxolane-4,5-dicarboxylic acid dimethyl ester

Refernces

• 1、 Liu, Na,Jensen, Anders A.,Bunch, Lennart. "β-Indolyloxy Functionalized Aspartate Analogs as Inhibitors of the Excitatory Amino Acid Transporters (EAATs)". . p. 2212 - 2220. Retrieved 2020.
• 2、 Hashimoto, Yuki,Michimuko, Chiaki,Yamaguchi, Koki,Nakajima, Makoto,Sugiura, Masaharu. "Selective Monoacylation of Diols and Asymmetric Desymmetrization of Dialkyl meso-Tartrates Using 2-Pyridyl Esters as Acylating Agents and Metal Carboxylates as Catalysts". . p. 9313 - 9321. Retrieved 2019/08/12.
• 3、 Zhu, Jie,Sun, Xiao-Tao,Wang, Xiao-Dong,Wu, Lei. "Enantioselective Dihydroxylation of Alkenes Catalyzed by 1,4-Bis(9-O-dihydroquinidinyl)phthalazine-Modified Binaphthyl–Osmium Nanoparticles". . p. 1788 - 1792. Retrieved 2018/04/30.