83540-97-0

Basic information

• Product Name: DIISOPROPYL (R)-(+)-MALATE
• Synonyms: DIISOPROPYL (R)-(+)-MALATE;(2R)-2-Hydroxybutanedioic acid 1,4-bis(1-methylethyl) ester;Diisopropyl (R)-(+)-2-hydroxysuccinate;Diisopropyl D-malate;(R)-Diisopropyl 2-hydroxysuccinate;Butanedioic acid,2-hydroxy-,1,4-bis(1-methylethyl) ester,(2R)-;-Diisopropyl 2-hydroxysuccinate
• CAS NO: 83540-97-0
• Molecular Formula: C₁₀H₁₈O₅
• Molecular Weight: 218.25
• Mol File: 83540-97-0.mol

Chemical Properties

• Boiling Point: 237 °C(lit.)
• Flash Point: >230 °F
• Appearance: /
• Density: 1.055 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.000105mmHg at 25°C
• Refractive Index: n20/D 1.43(lit.)
• Storage Temp.: 2-8°C
• PKA: 12.45±0.20(Predicted)
• CAS DataBase Reference: DIISOPROPYL (R)-(+)-MALATE(CAS DataBase Reference)
• NIST Chemistry Reference: DIISOPROPYL (R)-(+)-MALATE(83540-97-0)
• EPA Substance Registry System: DIISOPROPYL (R)-(+)-MALATE(83540-97-0)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 83540-97-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Diisopropyl (R)-(+)-Malate is used as a chiral reagent for the synthesis of pharmaceuticals. Its ability to create enantiomerically pure products is essential in the development of drugs with specific therapeutic effects, as the different enantiomers of a drug can have different biological activities.
Used in Agrochemical Industry:
Diisopropyl (R)-(+)-Malate is used as a chiral reagent in the production of agrochemicals. Its role in creating enantiomerically pure products is vital in the synthesis of pesticides and other agrochemicals, ensuring that the final product has the desired biological activity and minimizing potential side effects.
Used in Organic Synthesis:
Diisopropyl (R)-(+)-Malate is used as a reagent in the synthesis of various organic compounds. Its unique stereochemistry allows it to participate in reactions that require the formation of specific optical isomers, contributing to the development of new and improved synthetic materials.
Used in Research and Development:
Diisopropyl (R)-(+)-Malate is used as a research tool in the study of stereochemistry and enantioselective synthesis. Its properties make it an important compound for understanding the behavior of chiral molecules and developing new methods for the synthesis of enantiomerically pure products.

InChI:InChI=1/C10H18O5/c1-6(2)14-9(12)5-8(11)10(13)15-7(3)4/h6-8,11H,5H2,1-4H3/t8-/m0/s1

Upstream product

• 2217-15-4 L-(+)-diisopropyl tartrate 
• 636-61-3 D-Malic acid 
• 67-63-0 isopropyl alcohol 
• 371160-97-3 tert-butyl-[(2R,5S,6S)-5,6-dimethoxy-5,6-dimethyl-3-oxo-[1,4]dioxan-2-yl]-acetate 

Downstream Products

• 130713-47-2 2R-hydroxy-3S-(phenylmethyl)butanedioic acid 
• 355126-87-3 (2S,3R)-2-(4-Benzyloxy-3-methoxy-benzyl)-3-hydroxy-succinic acid diisopropyl ester 
• 117471-08-6 (R)-2-Benzyl-3-hydroxy-succinic acid diisopropyl ester 

Relevant articles and documents

Preparation of enantiopure butane-2,3-diacetals of glycolic acid and alkylation reactions leading to α-hydroxyacid and amide derivatives

The preparation of butane-2,3-diacetal protected glycolic acid and related systems is described together with highly selective alkylation reactions of (R,R) and (S,S) butanediacetal protected glycolic acid. These compounds are readily deprotected to give

Butane-2,3-diacetal-desymmetrized glycolic acid - A new building block for the stereoselective synthesis of enantiopure α-hydroxy acids

According to a chiral memory protocol, a chiral glycolic acid equivalent, the butane-2,3-diacetal-desymmetrized glycolate 2, is obtained from chiral 3-halopropane-1,2-diols 1. Compound 2 is a new and effective building block for the synthesis of mono- and

Synthesis of unnatural (R)-malates from L-tartrates

The cyclic thionocarbonates of L-tartrates were cleanly converted to (R)-malates by treating with magnesium iodide or magnesium and iodine.

Ruthenium-catalyzed production of cyclic sulfates

A ruthenium catalyzed method to synthesize cyclic sulfate compounds from the corresponding cyclic sulfites, and the cyclic sulfate reaction products obtained by this method. These cyclic sulfates further react with selected nucleophiles to give various substituted products. The method is an efficient means for the synthesis of chiral building blocks from tartaric acid enantiomers in high yields using an overall two-stage, one-pot reaction procedure. The chiral compounds can be transformed by nucleophilic reactions into chiral building blocks useful for the synthesis of natural biologically active products, such as antibiotics and pheromones.

Ruthenium-catalyzed production of cyclic sulfates

A ruthenium catalyzed method to synthesize cyclic sulfate compounds from the corresponding cyclic sulfites, and the cyclic sulfate reaction products obtained by this method. These cyclic sulfates further react with selected nucleophiles to give various substituted products. The method is an efficient means for the synthesis of chiral building blocks from tartaric acid enantiomers in high yields using an overall two-stage, one-pot reaction procedure. The chiral compounds can be transformed by nucleophilic reactions into chiral building blocks useful for the synthesis of natural biologically active products, such as antibiotics and pheromones.

A practical synthesis of D-malate esters from L-tartrate esters

D-malate esters were synthesized in one-pot from L-tartrate esters in 70-80% overall yields via the corresponding tartrate cyclic sulfites.

Cyclic sulfate compounds

A ruthenium catalyzed method to synthesize cyclic sulfate compounds from the corresponding cyclic sulfites, and the cyclic sulfate reaction products obtained by this method. These cyclic sulfates further react with selected nucleophiles to give various su

A HIGHLY EFFICIENT DEOXYDATION OF α-OXYGENATED ESTERS VIA SmI2-INDUCED ELECTRON TRANSFER PROCESS

A variety of α-oxygenated esters, such as α-acetoxy, α-methoxy-, α-OTPH, and α-hydroxy esters were easily reduced at room temperature to give the corresponding saturated esters in good to excellent yields with the aid of an efficient electron transfer system, SmI2-THF-HMPA.The method was succesfully applied to the direct conversion of (R,R)-tartrates to (R)-malates.

Enantioselective Syntheses of 3-Substituted 4-(Alkoxycarbonyl)-2-azetidinones from Malic Acid

Enantioselective syntheses of 3-substituted 4-(alkoxycarbonyl)-2-azetidinones from malic acid have been developed.Alkylation of diesters of D-malic acid provided primarily the erythro products 15RS.Base-mediated inversion gave racemic threo isomers 15.Saponification of 15 and selective monoesterification provided the correspondingly substituted β-hydroxy acids 17, which could also be epimerized at the hydroxyl position.Separate conversion of the isomers 17 to the hydroxamates 18 followed by cyclization gave the desired β-lactams 19 with complete control of stereochemistry.