Methyl (R)-(+)-lactate

Base Information

• Chemical Name: Methyl (R)-(+)-lactate
• CAS No.: 17392-83-5
• Molecular Formula: C4H8O3
• Molecular Weight: 104.106
• Hs Code.: 29181100
• European Community (EC) Number: 241-420-6
• UNII: 45MZ1T3TBV
• DSSTox Substance ID: DTXSID201045071
• Nikkaji Number: J208.669G
• Wikidata: Q27144784
• Mol file: 17392-83-5.mol

Synonyms:17392-83-5;Methyl (R)-(+)-lactate;(R)-Methyl 2-hydroxypropanoate;methyl D-lactate;Methyl (R)-lactate;methyl (2R)-2-hydroxypropanoate;(+)-Methyl D-lactate;Methyl D-(+)-Lactate;Methyl lactate, (+)-;(+)-methyl lactate;D-Lactic acid methyl ester;D-methyl lactate;(R)-methyl lactate;D-lactate methyl ester;Methyl-D-lactate;45MZ1T3TBV;Propanoic acid, 2-hydroxy-, methyl ester, (2R)-;EINECS 241-420-6;UNII-45MZ1T3TBV;methyl (R)-2-hydroxypropanoate;D-(+)-Lactic Acid Methyl Ester;methyl (2R)-2-oxidanylpropanoate;(2R)-2-hydroxypropanoic acid methyl ester;EC 241-420-6;methyl-(R)-lactate;(+)-methyl-d-lactate;methyl(R)-(+)-lactate;(R)-(+)-methyl lactate;METHYL LACTATE, D-;Methyl-D-2-hydroxypropionate;SCHEMBL63918;methyl (R)-(-+)-lactate;(R)-lactic acid methyl ester;(+)-lactic acid methyl ester;(R)-Methyl2-hydroxypropanoate;(R)-lactic acid, methyl ester;methyl(2r)-2-hydroxypropanoate;methyl (R)-2-hydroxypropionate;CHEBI:74611;methyl (2R)-2-hydroxypropionate;DTXSID201045071;(R)-(+)-lactic acid methyl ester;MFCD00004517;AKOS015902041;CS-W016638;(+)-METHYL 2-HYDROXYPROPANOATE;(+)-METHYL 2-HYDROXYPROPIONATE;(+)-2-hydroxypropanoic acid methyl ester;(+)-2-hydroxypropionic acid methyl ester;AS-12514;(R)-2-hydroxy-propanoic acid methyl ester;(R)-2-Hydroxy-propionic acid methyl ester;L0136;EN300-134403;F11215;A811586;A830360;J-010952;J-521716;Q27144784;(+)-Methyl D-lactate, 98%, optical purity ee: 96% (GLC)

Chemical Property of Methyl (R)-(+)-lactate

Chemical Property:

• Appearance/Colour: Colorless to light yellow liquid
• Vapor Pressure: 1.93mmHg at 25°C
• Melting Point: -66.2oC
• Refractive Index: n20/D 1.413(lit.)
• Boiling Point: 145.3 °C at 760 mmHg
• PKA: 13.07±0.20(Predicted)
• Flash Point: 47.1 °C
• PSA: 46.53000
• Density: 1.085 g/cm³
• LogP: -0.45980
• Storage Temp.: 2-8°C
• Water Solubility.: miscible, hydrolyses
• XLogP3: -0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 104.047344113
• Heavy Atom Count: 7
• Complexity: 69.3

Purity/Quality:

99% ^*data from raw suppliers

D-Methyl lactate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 10-36/37
• Safety Statements: 16-24-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(C(=O)OC)O
• Isomeric SMILES: C[C@H](C(=O)OC)O
• Uses: (+)-Methyl D-lactate can be used as a starting material in the asymmetric preparation of: Neomethymycin, a macrolide which contains 12-membered macrolactone that is used as a potent biological agent. PM-toxin A.It can also be used as a chiral pool along with D-(-)-tartaric acid in the stereoselective total synthesis of separacenes A and B via Trost-Rychnovsky alkyne rearrangement, Horner-Wadsworth-Emmons olefination as well as Corey-Bakshi-Shibata reaction.

Technology Process of Methyl (R)-(+)-lactate

There total 25 articles about Methyl (R)-(+)-lactate 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%

pyruvic acid methyl ester (600-22-6) → (R)-Methyl lactate (17392-83-5,2155-30-8)

Guidance literature:

With hydrogen; Cinchonidin; polyvinylpyrrolidone-stabilized platinum clusters; In acetic acid; at 25 ℃; for 0.5h; under 30002.4 Torr;

DOI:10.1016/S0040-4039(98)00088-4

Reference yield: 98.0%

methyl lactate (547-64-8,2155-30-8) → L-Lactic acid (79-33-4,106989-11-1,26811-96-1,31587-11-8,26100-51-6) + (R)-Methyl lactate (17392-83-5,2155-30-8)

Guidance literature:

With marine microbial esterase; In aq. phosphate buffer; at 37 ℃; for 1h; pH=7.5; pH-value; Temperature; Solvent; Reagent/catalyst; Time; enantioselective reaction; Resolution of racemate; Enzymatic reaction;

DOI:10.1016/S1872-2067(16)62495-6

Reference yield: 60.0%

methanol (67-56-1) + (S)-2-hydroxymethyl-N-((R)-2-hydroxy)-propanoyl pyrrolidine (170945-08-1) → (R)-Methyl lactate (17392-83-5,2155-30-8)

Guidance literature:

With sulfuric acid; Heating;

DOI:10.1016/S0040-4020(98)00914-4

upstream raw materials:

methanol

D-Lactic acid

diazomethane

(R)-(+)-2-acetoxypropionic acid

Downstream raw materials:

2-benzoyloxy-propionic acid methyl ester

methyl (2R)-2-methoxypropanoate

(S)-2-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxymethoxy)-propionic acid methyl ester

methyl (2R)-2-(benzyloxy)propanoate

Refernces

• 1、 Keilitz, Juliane,Nowag, Sabrina,Marty, Jean-Daniel,Haag, Rainer. "Chirally modified platinum nanoparticles stabilized by dendritic core-multishell architectures for the asymmetric hydrogenation of ethyl pyruvate". . p. 1503 - 1511. Retrieved 2010.
• 2、 Sharma, Poonam,Sharma, Rakesh K.. "Platinum functionalized multiwall carbon nanotube composites as recyclable catalyst for highly efficient asymmetric hydrogenation of methyl pyruvate". . p. 102481 - 102487. Retrieved 2015.
• 3、 Simons, K. E.,Ibbotson, A.,Johnston, P.,Plum, H.,Wells, P. B.. "Enantioselective Hydrogenation. III. Methyl Pyruvate Hydrogenation Catalyzed by Alkaloid-Modified Iridium". . p. 321 - 328. Retrieved 1994.
• 4、 Bhaduri, Sumit,Darshane, Vishnu S.,Sharma, Krishna,Mukesh, Doble. "Carbonyl Cluster Derived Polystyrene Supported Platinum for Asymmetric Hydrogenation of α-Ketoesters". . p. 1738 - 1740. Retrieved 1992.
• 5、 Collier, Paul J.,Hall, Tracey J.,Iggo, Jonathan A.,Johnston, Peter,Slipszenko, J. Anton,Wells, Peter B.,Whyman, Robin. "Solvent and substituent effects on the sense of the enantioselective hydrogenation of pyruvate esters catalysed by Pd and Pt in colloidal and supported forms". . p. 1451 - 1452. Retrieved 1998.
• 6、 Griffiths, Stephen P.,Johnston, Peter,Vermeer, Wilhelmus A. H.,Wells, Peter B.. "Novel Alkaloid Modifiers for Enantioselective Heterogeneous Catalysis". . p. 2431 - 2432. Retrieved 1994.
• 7、 Chen, Rong,Liu, Qinghai,Wang, Hualei,Wei, Dongzhi,Xie, Youyu,Yang, Zeyu,Ye, Wenjie. "Efficient Asymmetric Synthesis of Ethyl (S)-4-Chloro-3-hydroxybutyrate Using Alcohol Dehydrogenase SmADH31 with High Tolerance of Substrate and Product in a Monophasic Aqueous System". . p. 1068 - 1076. Retrieved 2020/07/06.
• 8、 Jiang, He-yan,Xu, Jie,Sun, Bin. "Enantioselective hydrogenation of α-ketoesters catalyzed by cinchona alkaloid stabilized Rh nanoparticles in ionic liquid". . p. 818 - 823. Retrieved 2019/08/07.