(2S,3R)-2-Hydroxy-3-methylsuccinic acid dimethyl ester

Base Information

• Chemical Name: (2S,3R)-2-Hydroxy-3-methylsuccinic acid dimethyl ester
• CAS No.: 73890-17-2
• Molecular Formula: C₇H₁₂O₅
• Molecular Weight: 176.169
• Mol file: 73890-17-2.mol

Synonyms:(2S,3R)-2-Hydroxy-3-methylbutanedioic acid dimethyl ester;(2S,3R)-2-Hydroxy-3-methylsuccinic acid dimethyl ester;(3R)-3-Methyl-L-malic acid dimethyl ester

Chemical Property of (2S,3R)-2-Hydroxy-3-methylsuccinic acid dimethyl ester

Chemical Property:

• PSA: 72.83000
• LogP: -0.67060
• Solubility.: Dichloromethane

Purity/Quality:

99% ^*data from raw suppliers

(2S,3R)-2-Hydroxy-3-methyl-butanedioicAcidDimethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,3R)-2-Hydroxy-3-methyl-butanedioic Acid Dimethyl Ester is an intermediate in synthesizing 5-Methyl-2’-deoxy Cytidine-13C,15N2 (M295904). It is an isotopic analog of 5-Methyl-2’-deoxy Cytidine (M295900), a Cytidine (C998300) analog and also an isostere of Thymidine (T412000).

Technology Process of (2S,3R)-2-Hydroxy-3-methylsuccinic acid dimethyl ester

There total 39 articles about (2S,3R)-2-Hydroxy-3-methylsuccinic acid dimethyl ester 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:

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

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

(E)-3-(methoxycarbonyl)-2-methyl-3-pentenoic acid

2,4-dimethyl-3-(methoxycarbonyl)-γ-butyrolactone

Downstream raw materials:

(2S,3S)-2-Methyl-3-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester

(2S,3R)-2-Methyl-3-((S)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester

(2S,3S)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester

(2S,3R)-2-Methyl-3-((R)-3,3,3-trifluoro-2-methoxy-2-phenyl-propionyloxy)-succinic acid dimethyl ester

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.