2-hydroxy-3-methylbutanedioate

Base Information

• Chemical Name: 2-hydroxy-3-methylbutanedioate
• CAS No.: 5380-37-0
• Molecular Formula: C₅H₈O₅
• Molecular Weight: 148.116
• Mol file: 5380-37-0.mol

Synonyms:

Chemical Property of 2-hydroxy-3-methylbutanedioate

Chemical Property:

• Vapor Pressure: 0.000161mmHg at 25°C

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-hydroxy-3-methylbutanedioate

There total 32 articles about 2-hydroxy-3-methylbutanedioate 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: 92.0%

(2S,3R)-2-Hydroxy-3-methylbernsteinsaeure-dimethylester (50460-80-5,64864-56-8,73889-80-2,77398-86-8,78512-74-0,89104-81-4,150024-71-8,73890-17-2) → (2S,3R)-3-methylmalic acid (85026-06-8,5380-36-9,5380-37-0)

Guidance literature:

(2S,3R)-2-Hydroxy-3-methylbernsteinsaeure-dimethylester; With potassium hydroxide; In tetrahydrofuran; methanol; at 20 ℃; for 24h; Inert atmosphere;

With hydrogenchloride; In tetrahydrofuran; methanol; water; pH=1;

DOI:10.1002/anie.200906311

Reference yield: 50.0%

(2R,3R)-(-)-threo-3-methylaspartic acid (86562-29-0) → (2R,3R)-threo-β-methylmalic acid (13398-40-8,5380-36-9,5380-37-0)

Guidance literature:

With sodium nitrite; In sulfuric acid; water; at 0 - 25 ℃;

DOI:10.1016/0040-4020(82)80081-1

Reference yield:

citraconic acid (498-23-7,7407-59-2) → (R)-(-)-citramalic acid (6236-10-8,2306-22-1) + (2R,3S)-3-methylmalic acid (152204-30-3,5380-36-9,5380-37-0)

Guidance literature:

With TETRACYCLINE; In water; at 37 ℃; for 142h; Title compound not separated from byproducts; Clostridium formicoaceticum, phosphate buffer;

DOI:10.1016/S0040-4020(01)85678-7

upstream raw materials:

(2S,3S)-3-methylaspartic acid

D,L-threo-β-methylaspartic acid

diisopropyl (2R,3S)-2-methyl-3-hydroxybutanedioate

dimethyl (2R,3S)-2-O-acetyl-3-methylmalate

Downstream raw materials:

(2S,3S)-2-methylpentane-1,3-diol

Refernces

• 1、 Jeyakanthan, Jeyaraman,Drevland, Randy M.,Gayathri, Dasara Raju,Velmurugan, Devadasan,Shinkai, Akeo,Kuramitsu, Seiki,Yokoyama, Shigeyuki,Graham, David E.. "Substrate specificity determinants of the methanogen homoaconitase enzyme: Structure and function of the small subunit". scheme or table. p. 2687 - 2696. Retrieved 2011/03/20.
• 2、 Eck, Richard,Simon, Helmut. "Preparation of Both Enantiomers of Malic and Citramalic Acid and Other Hydroxysuccinic Acid Derivatives by Stereospecific Hydrations of cis or trans 2-Butene-1,4-dioic Acids with Resting Cells of Clostridium formicoaceticum". . p. 13641 - 13654. Retrieved 2007/10/02.