Dimethyl d-tartrate

Base Information

• Chemical Name: Dimethyl d-tartrate
• CAS No.: 5057-96-5
• Molecular Formula: C₆H₁₀O₆
• Molecular Weight: 178.142
• European Community (EC) Number: 236-118-6
• Nikkaji Number: J135.635F
• Wikidata: Q106902858
• Mol file: 5057-96-5.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:

• Vapor Pressure: 0.000467mmHg at 25°C
• Melting Point: 57-60°C(dec.)(lit.)
• Refractive Index: 1.47
• 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: -1.16560
• 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 2,3-DIHYDROXYSUCCINATE 95.00% ^*data from reagent suppliers

Safty Information:

• Safety Statements: S24/25:

MSDS Files:

SDS file from LookChem

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 9 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: 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: 92.0%

methanol (67-56-1) + diethyl tartrate (21066-72-8) → dimethyl meso-tartrate (608-69-5,13171-64-7,117356-23-7,608-68-4,5057-96-5)

Guidance literature:

With di(n-butyl)tin oxide; In methanol; for 12h; Heating;

DOI:10.1002/1521-3773(20011001)40:19<3672::AID-ANIE3672>3.0.CO;2-Y

Reference yield: 88.0%

methanol (67-56-1) + meso-tartaric acid (147-73-9,138508-61-9) → dimethyl meso-tartrate (608-69-5,13171-64-7,117356-23-7,608-68-4,5057-96-5)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; for 20h; Reflux;

DOI:10.1039/c4ob01535e

upstream raw materials:

diazomethane

meso-tartaric acid

methanol

dimethyl cis-but-2-ene-1,4-dioate

Downstream raw materials:

dimethyl meso-2,3-O-benzylidenetartrate

4,5-trans-bis(methoxycarbonyl)-2-phenyl-1,3-dioxolan

(4R,5R)-2-ethyl-2-phenyl-1,3-dioxolane-4,5-dicarboxylic acid dimethyl ester

Methyl glyoxylate

Refernces

• 1、 Borrell, Margarida,Costas, Miquel. "Mechanistically Driven Development of an Iron Catalyst for Selective Syn-Dihydroxylation of Alkenes with Aqueous Hydrogen Peroxide". supporting information. p. 12821 - 12829. Retrieved 2017/09/25.
• 2、 Lukasik, Beata,Mikolajczyk, Marian,Bujacz, Grzegorz,Zurawiski, Remigiusz. "Synthesis and the absolute configuration of both enantiomers of 4,5-dihydroxy-3-(formyl)cyclopent-2-enone acetonide as a new chiral building block for prostanoid synthesis". . p. 807 - 816. Retrieved 2015/02/19.