196605-90-0

Usage

Uses

Used in Pharmaceutical and Agrochemical Industries:
(S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol is utilized as a chiral building block in the synthesis of various pharmaceuticals and agrochemicals. Its optical purity and specific spatial arrangement enable the creation of enantiomerically pure compounds, which are essential for the development of effective and safe drugs and agrochemicals.
Used in Asymmetric Catalysis:
(S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol also serves as a ligand in asymmetric catalysis, a process that promotes enantioselective reactions. As a ligand, (S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol enhances the selectivity of catalysts, leading to the production of desired enantiomers with higher yields and purity. This application is crucial in the synthesis of chiral molecules, which are prevalent in the pharmaceutical, agrochemical, and fragrance industries.
Used in Advanced Materials and Fine Chemicals Production:
Due to its unique stereochemistry and reactivity, (S,S)-(+)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diol has potential applications in the production of advanced materials and fine chemicals. Its ability to form specific spatial arrangements and interact with other molecules makes it a promising candidate for the development of novel materials with tailored properties for various high-value applications.

Upstream product

• 52988-36-0 triphenyl(3,5-dimethylbenzyl)phosphonium bromide 
• 27129-86-8 1-bromomethyl-3,5-dimethylbenzene 
• 5779-95-3 3,5-dimethylbenzaldehyde 
• 13863-27-9 (E)-1,2-bis(3,5-dimethylphenyl)ethene 
• 101789-41-7 1,2-bis(3,5-dimethylphenyl)ethane-1,2-dione 

Downstream Products

• 866044-17-9 (1R,2R)-1,2-N,N'-bis(p-toluenesulfonylamino)-1,2-bis(3,5-dimethylphenyl)ethane 
• 866044-13-5 (R,R)-1,2-diazido-1,2-bis(3,5-dimethylphenyl)ethane 
• 503112-15-0 (1R,2R)-1,2-bis(3,5-dimethylphenyl)ethane-1,2-diamine 

Relevant academic research and scientific papers

Catalytic Syn-Selective Nitroaldol Approach to Amphenicol Antibiotics: Evolution of a Unified Asymmetric Synthesis of (-)-Chloramphenicol, (-)-Azidamphenicol, (+)-Thiamphenicol, and (+)-Florfenicol

A unified strategy for an efficient and high diastereo- and enantioselective synthesis of (-)-chloramphenicol, (-)-azidamphenicol, (+)-thiamphenicol, and (+)-florfenicol based on a key catalytic syn-selective Henry reaction is reported. The stereochemistry of the ligand-enabled copper(II)-catalyzed aryl aldehyde Henry reaction of nitroethanol was first explored to forge a challenging syn-2-amino-1,3-diol structure unit with vicinal stereocenters with excellent stereocontrol. Multistep continuous flow manipulations were carried out to achieve the efficient asymmetric synthesis of this family of amphenicol antibiotics.

Catalytic enantioselective and catalyst-controlled diastereofacial- selective additions of allyl- and crotylboronates to aldehydes using chiral Bronsted acids

(Chemical Equation Presented) Towards the ideal: A chiral diol-SnCl 4 complex is applied to the allylboration of aldehydes (see scheme). This approach highlights the use of chiral Bronsted acid catalysis in the development of an ideal method for the allylation of aldehydes which would display high diastereo- and enantioselectivity, wide substrate scope, and high practicality (ease of use, low cost, and low environmental impact).

Chiral bis(N-sulfonylamino)phosphine- and TADDOL-phosphite-oxazoline ligands: Synthesis and application in asymmetric catalysis

A series of N,P-ligands has been prepared, containing a chiral oxazoline ring and as a second chiral unit a bis(N-sulfonylamino)phosphine group embedded in a diazaphospholidine ring or a cyclic phosphite group derived from TADDOL. These modular ligands are readily synthesized from chiral amino alcohols and chiral 1,2-diamines or TADDOLs. Palladium and iridium complexes derived from these ligands were found to be efficient catalysts for enantioselective allylic alkylation and olefin hydrogenation, respectively.

Oxazaborolidine-mediated asymmetric reduction of 1,2-diaryl-2- benzyloxyiminoethanones and 1,2-diarylethanediones

Highly enantioselective reduction of 1,2-diaryl-2- benzyloxyiminoethanones and 1,2-diarylethanediones was conducted using oxazaborolidine derived from L-threonine and borane complexes to give β- imino alcohols and 1,2-diaryl-1,2-ethanediols in high enantiomeric purity. Subsequent reduction of the imino functionality of the former products afforded either syn- or anti-2-amino-1,2-diarylethanols in high enantiomeric purity by choosing appropriate reduction methods.