Dimethyl L-tartrate

Base Information

• Chemical Name: Dimethyl L-tartrate
• CAS No.: 608-68-4
• Deprecated CAS: 117356-23-7,72718-98-0,89599-43-9
• Molecular Formula: C6H10O6
• Molecular Weight: 178.142
• Hs Code.: 29181300
• European Community (EC) Number: 210-166-8
• DSSTox Substance ID: DTXSID50883209
• Nikkaji Number: J127.927K
• Wikidata: Q72472102
• Mol file: 608-68-4.mol

Synonyms:(+)-Dimethyl L-tartrate;608-68-4;Dimethyl L-tartrate;(2R,3R)-dimethyl 2,3-dihydroxysuccinate;Dimethyl L-(+)-Tartrate;L-(+)-Tartaric acid dimethyl ester;L-DIMETHYL TARTRATE;Dimethyl (+)-tartrate;dimethyl (2R,3R)-2,3-dihydroxybutanedioate;Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, 1,4-dimethyl ester;NSC 517;EINECS 210-166-8;Butanedioic acid, 2,3-dihydroxy- (2R,3R)-, dimethyl ester;MFCD00064437;1,4-dimethyl (2R,3R)-2,3-dihydroxybutanedioate;Dimethyl (R(R*,R*))-tartrate;Dimethyl [R(R*,R*)]-tartrate;l-Tartaric acid, dimethyl ester;Dimethyl 2,3-dihydroxysuccinate #;Butanedioic acid, 2,3-dihydroxy- [R-(R*,R*)]-, dimethyl ester;L-(+)-Tartaric acid, dimethyl ester;(+)-DIMETHYL-L-TARTRATE;Dimethyl (2S,3S)-2,3-Dihydroxysuccinate;dimethyl (2R,3R)-2,3-dihydroxysuccinate;L-DMT;dimethyl L(+)-tartrate;( )-Dimethyl L-tartrate;SCHEMBL590895;L-Tartaric acid dimethyl ester;LCZC1826;Dimethyl-L-(+)-Tartratic Acid;DTXSID50883209;L(+)tartaric acid dimethyl ester;(+)-Dimethyl L-tartrate, 99%;5057-96-5;STR02392;Tartaric acid, dimethyl ester, ()-;AKOS015894938;AC-3434;CS-0093793;T0006;F20334;EN300-1703345;(+)-Dimethyl L-tartrate, purum, >=99.0% (sum of enantiomers, GC)

Chemical Property of Dimethyl L-tartrate

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Melting Point: 48-50 °C
• Refractive Index: 21 ° (C=2.5, 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
• Water Solubility.: Soluble in water.
• 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 L-tartrate ^*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

Useful:

• Chemical Classes: Other Classes -> Esters, Other
• Canonical SMILES: COC(=O)C(C(C(=O)OC)O)O
• Isomeric SMILES: COC(=O)[C@@H]([C@H](C(=O)OC)O)O
• Uses: (+)-Dimethyl L-tartrate is used as a starting reagent in the synthesis of (+)-Monomorine I, a pyrrolidine-based alkaloid that is a trail pheromone of the Pharaoh’s ant (Monomorium pharaonis). (+)-Dimethyl L-tartrate can react with sulfur tetrafluoride to form dimethyl meso-2,3-difluorosuccinate.It may be used in the synthesis of the following chiral ligands for use in asymmetric synthesis:(2R, 3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butanediol(-)-(4S,5R)-4-(2-pyridyl)-5-(diphenylphosphino)methyl-2,2-dimethyl-1,3-dioxolane (PYDIPHOS)(4R,5R)-α,α,α′,α′-2,2-hexaphenyl-4,5-dimethanol-1,3-dioxolane

Technology Process of Dimethyl L-tartrate

There total 27 articles about Dimethyl L-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) + L-Tartaric acid (87-69-4,138508-61-9) → dimethyl L-tartrate (608-68-4)

Guidance literature:

With toluene-4-sulfonic acid; In toluene;

DOI:10.1002/chir.22814

Reference yield: 97.0%

L-Tartaric acid (87-69-4,138508-61-9) + trimethyl orthoformate (149-73-5) → dimethyl L-tartrate (608-68-4)

Guidance literature:

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

DOI:10.1007/s00706-013-1100-x

Reference yield: 90.5%

methanol (67-56-1) + L-Tartaric acid (87-69-4,138508-61-9) + trimethyl orthoformate (149-73-5) → dimethyl L-tartrate (608-68-4)

Guidance literature:

With acetyl chloride; for 6h; Heating;

upstream raw materials:

diazomethane

meso-tartaric acid

methanol

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

Downstream raw materials:

dimethyl 2,3-O-benzylidene-L-tartrate

N,N'-diallyl-tartramide

dimethyl meso-2,3-O-benzylidenetartrate

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

Refernces

• 1、 Pilon, Simone,Ingemann J?rgensen, Steen,van Maarseveen, Jan H.. "[2]Catenane Synthesis via Covalent Templating". . p. 2310 - 2314. Retrieved 2021/01/20.
• 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.