83541-68-8

Basic information

• Product Name: (-)-DIISOPROPYL-L-MALATE
• Synonyms: L-MALIC ACID DIISOPROPYL ESTER;DIISOPROPYL (S)-(-)-MALATE;(-)-DIISOPROPYL-L-MALATE;DIISOPROPYL L-MALATE;(S)-2-Hydroxybutanedioic acid diisopropyl ester;(S)-2-Hydroxysuccinic acid diisopropyl ester;[S,(-)]-2-Hydroxysuccinic acid diisopropyl ester
• CAS NO: 83541-68-8
• Molecular Formula: C₁₀H₁₈O₅
• Molecular Weight: 218.25
• Product Categories: Chiral Building Blocks;Esters;Organic Building Blocks
• Mol File: 83541-68-8.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 237 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.055 g/mL at 25 °C(lit.)
• Vapor Pressure: 5.75E-05mmHg at 25°C
• Refractive Index: n20/D 1.43(lit.)
• CAS DataBase Reference: (-)-DIISOPROPYL-L-MALATE(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-DIISOPROPYL-L-MALATE(83541-68-8)
• EPA Substance Registry System: (-)-DIISOPROPYL-L-MALATE(83541-68-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 83541-68-8(Hazardous Substances Data)

Usage

Description

(-)-DIISOPROPYL-L-MALATE, also known as Diisopropyl (S)-(-)-malate, is an organic compound that serves as a crucial intermediate in the synthesis of various bioactive compounds. It is characterized by its unique structure, which includes two isopropyl groups and a malate moiety, and plays a significant role in the development of pharmaceuticals and other related applications.

Uses

Used in Pharmaceutical Industry:
(-)-DIISOPROPYL-L-MALATE is used as a starting material for the total synthesis of (-)-Wikstromol, an α-hydroxylated lactone lignan that can be found in Asian medicinal plants. (-)-DIISOPROPYL-L-MALATE possesses potential therapeutic properties, making it a valuable component in the development of new drugs and treatments.
As a key intermediate in the synthesis of bioactive compounds, (-)-DIISOPROPYL-L-MALATE can be utilized in various other applications within the pharmaceutical industry, such as the development of novel drug candidates, enhancement of drug delivery systems, and improvement of existing medications. Its unique structure and properties make it a promising building block for the creation of innovative and effective pharmaceutical products.

InChI:InChI=1/C10H18O5/c1-6(2)10(9(13)14,5-8(11)12)15-7(3)4/h6-7H,5H2,1-4H3,(H,11,12)(H,13,14)/p-2/t10-/m0/s1

Upstream product

• 127854-45-9 (4S,5S)-2,2-Dioxo-2λ⁶-[1,3,2]dioxathiolane-4,5-dicarboxylic acid diisopropyl ester 
• 62961-64-2 D-(-)-diisopropyl tartrate 
• 75-30-9 2-iodo-propane 
• 97-67-6 (S)-Malic acid 
• 67-63-0 isopropyl alcohol 

Downstream Products

• 586972-81-8 2R-[3-(4-ethoxy-phenyl)-propyl]-3S-hydroxy-succinic acid diisopropylester 
• 363139-49-5 (2R,3S)-2-Hydroxy-3-(3-methoxy-benzyl)-succinic acid diisopropyl ester 
• 336101-52-1 (2R,3S)-2-[4-(benzyloxy)-3-methoxybenzyl]-3-hydroxybutanedioic acid diisopropyl ester 

Relevant articles and documents

Process for the preparation of (4R,6S)-4-hydroxy-6-hydroxymethyl-tetrahydropyran-2-one

The present invention relates to an improved, efficient and enantio-selective process for the synthesis of (4R, 6S)-4-hydroxy-6-hydroxymethyl tetrahydropyran-2-one, employing the Sharpless asymmetric dihydroxylation and regiospecific nucleophilic hydride opening of the cyclic sulfite/sulfate as the key steps. The invention also resides in the intermediates used in the process.

Further Synthesis of Optically Active Verrucarinic Acid

Two new syntheses of verrucarinic acid ((2S,3R)-2,5-dihydroxy-3-methylpentanoic acid) and its derivatives, suitably protected for the further conversion to macrocyclic trichothecenes, are described.The first one makes use of a diastereoselective alkylation of a (-)-(S)-malic acid ester and the regioselective reduction of one carboxyl function to a methyl group.The second approach involves a stereoselective addition of an allylsilane to a chiral glyoxylate.