104333-83-7

Basic information

• Product Name: (2R,3R)-2,3-O-(1-PHENYLETHYLIDENE)-L-TARTARIC ACID DIMETHYL ESTER
• Synonyms: (2R,3R)-2,3-O-(1-PHENYLETHYLIDENE)-L-TARTARIC ACID DIMETHYL ESTER;DIMETHYL (2R,3R)-2,3-O-(1-PHENYLETHYLIDENE)-L-TARTRATE;DIMETHYL (4R,5R)-2-METHYL-2-PHENYL-1,3-DIOXOLANE-4,5-DICARBOXYLATE;Phenylethylidenetartaricaciddimethylester;Dimethyl (4R,5R)-2-Methyl-2-phenyl-1,3-dioxolane-4,5-dicarboxylate (2R,3R)-2,3-O-(1-Phenylethylidene)-L-tartaric Acid Dimethyl Ester
• CAS NO: 104333-83-7
• Molecular Formula: C₁₄H₁₆O₆
• Molecular Weight: 280.27
• Product Categories: Chiral Building Blocks;Dioxanes & Dioxolanes;Dioxolanes;Esters (Chiral);Synthetic Organic Chemistry
• Mol File: 104333-83-7.mol
• Article Data: 5

Chemical Properties

• Melting Point: 54.0 to 58.0 °C
• Boiling Point: 359.2°C at 760 mmHg
• Flash Point: 156.8°C
• Appearance: /
• Density: 1.225g/cm³
• Vapor Pressure: 2.42E-05mmHg at 25°C
• Refractive Index: 1.506
• CAS DataBase Reference: (2R,3R)-2,3-O-(1-PHENYLETHYLIDENE)-L-TARTARIC ACID DIMETHYL ESTER(CAS DataBase Reference)
• NIST Chemistry Reference: (2R,3R)-2,3-O-(1-PHENYLETHYLIDENE)-L-TARTARIC ACID DIMETHYL ESTER(104333-83-7)
• EPA Substance Registry System: (2R,3R)-2,3-O-(1-PHENYLETHYLIDENE)-L-TARTARIC ACID DIMETHYL ESTER(104333-83-7)

Safety Data

• Hazardous Substances Data: 104333-83-7(Hazardous Substances Data)

Usage

General Description

(2R,3R)-2,3-O-(1-PHENYLETHYLIDENE)-L-TARTARIC ACID DIMETHYL ESTER is a chemical compound that is composed of two enantiomers of L-tartaric acid, which is a naturally occurring organic acid. It is commonly used as a chiral resolving agent in organic chemistry for the separation of racemic mixtures. The compound is also used in the synthesis of various pharmaceuticals and agrochemicals. It has a wide range of applications in industries such as pharmaceuticals, food, and agriculture. This chemical is important in the field of chemistry for its role in asymmetric synthesis and chiral separation processes.

InChI:InChI=1/C14H16O6/c1-14(9-7-5-4-6-8-9)19-10(12(15)17-2)11(20-14)13(16)18-3/h4-8,10-11H,1-3H3/t10-,11-/m1/s1

Upstream product

• 608-68-4 dimethyl L-tartrate 
• 4316-35-2 acetophenone dimethyl acetal 
• 98-86-2 acetophenone 

Downstream Products

• 109306-21-0 (4R-trans)-2-methyl-2-phenyl-α,α,α',α'-tetraphenyl-1,3-dioxolan-4,5-dimethanol 

Relevant articles and documents

TADDOL-TiCl2 catalyzed Diels-Alder reactions: Unexpected influence of the substituents in the 2-position of the dioxolane ring on the stereoselectivity

Several α,α,α',α'-tetra(3,5-dimethylphenyl)-1,3-dioxolane-4,5-dimethanols have been synthesized, and their TiCl2 derivatives used as catalysts in the reaction of cyclopentadiene with (E)-2-butenoyl-1,3-oxazolidin-2-one. The substituents in the 2-position of the dioxolane ring exert a decisive influence on the extent and direction of the asymmetric induction and, consequently any possible enantiomer of the cycloadducts can be preferentially obtained by changing these substituents. Molecular mechanics calculations of the structures and relative energies of the possible dienophile-catalyst complexes offer a tentative explanation for the results described.

Asymmetric Diels-Alder Reaction Catalyzed by a Chiral Titanium Reagent

A highly enantioselective Diels-Alder reaction has been developed by employing a chiral titanium reagent generated in situ from dichlorodiisopropoxytitanium and the chiral diol 1d, which is easily derived from tartaric acid.With a catalytic amount of the

ASYMMETRIC DIELS-ALDER REACTION PROMOTED BY A CHIRAL TITANIUM REAGENT

The asymmetric Diels-Alder reaction between prochiral dienes and dienophiles prepared from α,β-unsaturated acids and 1,3-oxazolidin-2-one proceeds by the use of a chiral alkoxy titanium(IV) to give the corresponding cycloadducts in high enantioselectivity