(R)-2-hydroxy-3,3-dimethylbutanoic acid

Base Information

• Chemical Name: (R)-2-hydroxy-3,3-dimethylbutanoic acid
• CAS No.: 22146-57-2
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• Hs Code.: 2918990090
• European Community (EC) Number: 889-837-8
• Nikkaji Number: J1.665.952E
• Mol file: 22146-57-2.mol

Synonyms:(R)-2-hydroxy-3,3-dimethylbutanoic acid;22146-57-2;(2R)-2-hydroxy-3,3-dimethylbutanoic acid;(R)-TRIMETHYLLACTIC ACID;(R)-Trimethyllacticacid;(R)-(-)-3,3-Dimethyl-2-hydroxybutyric acid;SCHEMBL2035324;FWVNWTNCNWRCOU-BYPYZUCNSA-N;MFCD00211269;AKOS006377035;(2R)-hydroxy-3,3-dimethylbutyric acid;(R)-2-Hydroxy-3,3-dimethylbutanoicacid;(r)-3,3-dimethyl-2-hydroxybutyric acid;2(R)-Hydroxy-3,3-dimethylbutanoic acid;(2R)-3,3-Dimethyl-2-hydroxybutyric acid;(2R)-2-hydroxy-3, 3-dimethylbutanoic acid;CS-0436719;F79704;EN300-1132068;A815971

Chemical Property of (R)-2-hydroxy-3,3-dimethylbutanoic acid

Chemical Property:

• Vapor Pressure: 0.00583mmHg at 25°C
• Refractive Index: 1.459
• Boiling Point: 242.4 °C at 760 mmHg
• Flash Point: 114.6 °C
• PSA: 57.53000
• Density: 1.1 g/cm³
• LogP: 0.47800
• Storage Temp.: 2-8°C
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 112

Purity/Quality:

99.3% ^*data from raw suppliers

(R)-Trimethyllacticacid 95 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

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

Technology Process of (R)-2-hydroxy-3,3-dimethylbutanoic acid

There total 10 articles about (R)-2-hydroxy-3,3-dimethylbutanoic acid 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: 86.0%

(s)-3,3-dimethyl-2-hydroxybutyric acid ethyl ester → (2R)-3,3-Dimethyl-2-hydroxybutyric acid (22146-57-2,851866-86-9)

Guidance literature:

With sodium hydroxide; In water; for 1.25h;

Reference yield: 81.0%

D-tert-leucine (26782-71-8) → (2R)-3,3-Dimethyl-2-hydroxybutyric acid (22146-57-2,851866-86-9)

Guidance literature:

With sulfuric acid; sodium nitrite; In water; at 0 - 23 ℃;

DOI:10.1016/j.bmc.2014.01.017

Reference yield:

trimethylpyruvic acid (815-17-8) → (2R)-3,3-Dimethyl-2-hydroxybutyric acid (22146-57-2,851866-86-9)

Guidance literature:

With hydrogen; 1,1'-dibenzyl-4,4'-bipyridinium; In water; at 35 ℃; under 760 Torr; biosynthesis by Proteus vulgaris (potassium phosphate buffer pH 7.0);

DOI:10.1016/S0040-4020(01)86506-6

upstream raw materials:

3,3-dimethyl-butan-2-one

L-tert-Leucine

trimethylpyruvic acid

1,1-dibromo-3,3-dimethylbutan-2-one

Downstream raw materials:

[4-Chloro-2-({[(S)-1-((R)-2-hydroxy-3,3-dimethyl-butyryl)-azetidine-2-carbonyl]-amino}-methyl)-benzyl]-carbamic acid tert-butyl ester

[4-Chloro-2-({[(S)-1-((R)-2-hydroxy-3,3-dimethyl-butyryl)-pyrrolidine-2-carbonyl]-amino}-methyl)-benzyl]-carbamic acid tert-butyl ester

(3S)-N-[5-chloro-2-(1H-tetrazol-1-yl)benzyl]-2-[(2R)-2-hydroxy-3,3-dimethylbutanoyl]pyrazolidine-3-carboxamide

(3S)-N-[5-chloro-2-(1H-tetrazol-1-yl)benzyl]-2-[(2R)-2-hydroxy-3,3-dimethylbutanoyl]isoxazolidine-3-carboxamide

Refernces

• 1、 Xu, Zhixiang,Yin, Wei,Martinelli, Leonardo K.,Evans, Joanna,Chen, Jinglei,Yu, Yang,Wilson, Daniel J.,Mizrahi, Valerie,Qiao, Chunhua,Aldrich, Courtney C.. "Reaction intermediate analogues as bisubstrate inhibitors of pantothenate synthetase". . p. 1726 - 1735. Retrieved 2014/03/21.
• 2、 Nelson, Todd D.,LeBlond, Carl R.,Frantz, Doug E.,Matty, Louis,Mitten, Jeffrey V.,Weaver, Damian G.,Moore, Jeffrey C.,Kim, Jaehon M.,Boyd, Russell,Kim, Pei-Yi,Gbewonyo, Kodzo,Brower, Mark,Sturr, Michael,McLaughlin, Kathleen,McMasters, Daniel R.,Kress, Michael H.,McNamara, James M.,Dolling, Ulf H.. "Stereoselective synthesis of a potent thrombin inhibitor by a novel P2-P3 lactone ring opening". . p. 3620 - 3627. Retrieved 2007/10/03.