dimethyl 2-hydroxy-3-methylbutanedioate

Base Information

• Chemical Name: dimethyl 2-hydroxy-3-methylbutanedioate
• CAS No.: 50460-80-5
• Molecular Formula: C₇H₁₂O₅
• Molecular Weight: 176.169
• Mol file: 50460-80-5.mol

Synonyms:dimethyl 2-hydroxy-3-methylbutanedioate

Chemical Property of dimethyl 2-hydroxy-3-methylbutanedioate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl 2-hydroxy-3-methylbutanedioate

There total 40 articles about dimethyl 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: 97.0%

dimethyl (S)-malate (617-55-0) + methyl iodide (74-88-4) → (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)

Guidance literature:

dimethyl (S)-malate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1.5h; Inert atmosphere;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 4h; Inert atmosphere;

DOI:10.5012/bkcs.2013.34.5.1371

Reference yield: 86.0%

dimethyl (S)-malate (617-55-0) + methyl iodide (74-88-4) → (2S)-2-Hydroxy-3-methyl-bernsteinsaeuredimethylester (50460-80-5,64864-56-8,73889-80-2,73890-17-2,77398-86-8,78512-74-0,89104-81-4,150024-71-8)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 5h;

DOI:10.1016/j.tetlet.2005.12.012

Reference yield: 71.0%

dimethyl (S)-malate (617-55-0) + methyl iodide (74-88-4) → (2S,3S)-2-Hydroxy-3-methyl-bernsteinsaeuredimethylester (50460-80-5,64864-56-8,73890-17-2,77398-86-8,78512-74-0,89104-81-4,150024-71-8,73889-80-2) + (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)

Guidance literature:

dimethyl (S)-malate; With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h;

methyl iodide; In tetrahydrofuran; at -78 ℃; for 5h;

DOI:10.1016/j.tetasy.2013.12.004

upstream raw materials:

diazomethane

Elaiophylin

(S)-2-Eth-(E)-ylidene-3-methyl-succinic acid dimethyl ester

(S)-2-Eth-(E)-ylidene-3-methyl-succinic acid 1-methyl ester

Downstream raw materials:

(2S,3S)-2,3-Epoxy-2-methylbernsteinsaeure-dimethylester

(2R,3S)-2,3-Epoxy-2-methylbernsteinsaeure-dimethylester

dimethyl (2S,3R)-3-methyl-2-O-tosylmalate

C₂₁H₂₈O₄

Refernces

• 1、 Kamal, Ahmed,Balakrishna, Moku,Reddy, Papagari Venkat,Rahim, Abdul. "First total synthesis of the E- and Z-isomers of cytospolide-D". . p. 148 - 155. Retrieved 2014/02/14.
• 2、 Paterson, Ian,Anderson, Edward A.,Dalby, Stephen M.,Lim, Jong Ho,Maltas, Philip,Loiseleur, Olivier,Genovino, Julien,Moessner, Christian. "The stereocontrolled total synthesis of spirastrellolide A methyl ester. Expedient construction of the key fragments". supporting information; scheme or table. p. 5861 - 5872. Retrieved 2012/08/28.