Ethyl 2-hydroxy-4-methylvalerate, (2R)-

Base Information

• Chemical Name: Ethyl 2-hydroxy-4-methylvalerate, (2R)-
• CAS No.: 60856-83-9
• Molecular Formula: C8H16O3
• Molecular Weight: 160.213
• Hs Code.: 2918199090
• UNII: Y39C7U1A75
• Nikkaji Number: J84.205B
• Wikidata: Q27294216
• Mol file: 60856-83-9.mol

Synonyms:60856-83-9;Ethyl 2-hydroxy-4-methylvalerate, (2R)-;Ethyl leucate, (+)-;Ethyl D-2-hydroxyisocaproate;ethyl (2R)-2-hydroxy-4-methylpentanoate;Ethyl 2-hydroxyisocaproate, (R)-;(R)-(+)-Ethyl Leucate;UNII-Y39C7U1A75;Ethyl 2-hydroxy-4-methylpentanoate, (+)-;Y39C7U1A75;Pentanoic acid, 2-hydroxy-4-methyl-, ethyl ester, (2R)-;Pentanoic acid, 2-hydroxy-4-methyl-, ethyl ester, (R)-;Ethyl D-Leucate;ethyl-D-leucate;ethyl-(R)-leucate;SCHEMBL3619291;(R)-Ethyl2-hydroxy-4-methylpentanoate;(2R)-ethyl 2-hydroxy-4-methylvalerate;(R)-Ethyl 2-hydroxy-4-methylpentanoate;(r)-2-hydroxy-4-methylpentanoic acid ethyl ester;Q27294216

Chemical Property of Ethyl 2-hydroxy-4-methylvalerate, (2R)-

Chemical Property:

• Vapor Pressure: 0.0967mmHg at 25°C
• Refractive Index: 1.434
• Boiling Point: 197.4 °C at 760 mmHg
• Flash Point: 74 °C
• PSA: 46.53000
• Density: 0.986 g/cm³
• LogP: 0.95650
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 160.109944368
• Heavy Atom Count: 11
• Complexity: 121

Purity/Quality:

99% ^*data from raw suppliers

(R)-(+)-EthylLeucate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CC(C)C)O
• Isomeric SMILES: CCOC(=O)[C@@H](CC(C)C)O
• Uses: (R)-(+)-Ethyl Leucate is used for the synthesis of optically active forms of Ipsenol, the pheromone of Ips bark beetles.

Technology Process of Ethyl 2-hydroxy-4-methylvalerate, (2R)-

There total 9 articles about Ethyl 2-hydroxy-4-methylvalerate, (2R)- 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:

ethanol (64-17-5) + (R)-2-hydroxy-4-methylpentanoic acid (20312-37-2,498-36-2) → (R)-ethyl 4-methyl-2-hydroxypentanoate (60856-83-9)

Guidance literature:

With hydrogenchloride;

DOI:10.1016/0040-4020(76)85032-6

Reference yield:

ethyl 4-methyl-2-oxopentanoate (26073-09-6) → ethyl (S)-2-hydroxy-4-methylpentanoate (60856-85-1) + (R)-ethyl 4-methyl-2-hydroxypentanoate (60856-83-9)

Guidance literature:

With potassium 9-O-(1,2:5,6-di-O-isopropylidene-α-D-glucofuranosyl)-9-boratabicyclo<3.3.1>nonane; In tetrahydrofuran; at -78 ℃; for 6h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00241a021

Reference yield:

1,1-Diethoxy-4-methyl-pent-1-ene → ethyl (S)-2-hydroxy-4-methylpentanoate (60856-85-1) + (R)-ethyl 4-methyl-2-hydroxypentanoate (60856-83-9)

Guidance literature:

With AD-mix-α; methanesulfonamide; In tert-butyl alcohol; at 0 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1002/anie.199702531

upstream raw materials:

ethanol

(R)-2-hydroxy-4-methylpentanoic acid

acetate of ethyl-(+/-)-leucinate

ethyl 4-methyl-2-oxopentanoate

Refernces

• 1、 Kirschning, Andreas,Draeger, Gerald,Jung, Alexander. "A New Asymmetric Formylation of Aldehydes". . p. 253 - 255. Retrieved 2007/10/03.
• 2、 Brown, Herbert C.,Ramachandran, P. Veeraraghavan,Weissman, Steven A.,Swaminathan, S.. "Selective Reductions. 46. Effect of the Steric Requirement at the 2-Position of Apopinene on chiral Reductions. B-(Iso-2-ethylapopinocampheyl)- and B-(Iso-2-n-propylapopinocampheyl)-9-borabicyclononanes as Improved Reagents for the Chiral Reduction of α,β-Acetylenic Ketones ...". . p. 6328 - 6333. Retrieved 2007/10/02.