143329-85-5

Usage

Uses

Used in Pharmaceutical Synthesis:
(R,R)-α,α'-dimethyl-2,6-pyridinedimethanol is used as a chiral resolving agent for the synthesis of pharmaceuticals and other chiral compounds. Its ability to selectively interact with other chiral molecules makes it a valuable tool in the development of new drugs and medicines.
Used in Catalysts:
(R,R)-α,α'-dimethyl-2,6-pyridinedimethanol is also utilized as a catalyst in the reduction of ketones and imines. Its chiral nature allows for the selective reduction of these functional groups, which is crucial in the production of specific enantiomers with desired biological activities.
Used in Medicinal Research:
(R,R)-α,α'-dimethyl-2,6-pyridinedimethanol has been studied for its potential neuroprotective and antioxidant properties. These characteristics make it a compound of interest in medicinal and biochemical research, where it could potentially be used in the development of treatments for neurological disorders and conditions related to oxidative stress.
Used in Chemical Synthesis:
In the broader field of chemical synthesis, (R,R)-α,α'-dimethyl-2,6-pyridinedimethanol serves as a versatile building block for the creation of various complex molecules. Its unique structure and reactivity contribute to its utility in organic chemistry and the synthesis of novel compounds with specific applications.

Upstream product

• 1129-30-2 2,6-Diacetylpyridine 
• 143329-89-9 α,α'-dihydroxy-1,3-diethylpyridine 

Downstream Products

• 923930-93-2 2-((S)-1-hydroxyethyl)-6-[(S)-1-(p-toluenesulfonyloxy)ethyl]pyridine 
• 175025-14-6 (S,S)-2,6-bis((α-p-toluenesulfonyloxy)ethyl)pyridine 
• 923930-95-4 2-{(R)-1-[(R)-1-phenylethyl]aminoethyl}-6-[(S)-1-(p-toluenesulfonyloxy)ethyl]pyridine 
• 923930-92-1 2-((S)-1-hydroxyethyl)-6-{(R)-1-[(R)-1-phenylethyl]aminoethyl}pyridine 

Relevant academic research and scientific papers

Autocatalytic Asymmetric Reduction of 2,6-Diacetylpyridine

(Formula presented). We report here that the C2-symmetric diol 2,6-bis(1-hydroxyethyl)pyridine (2) can effect chiral-catalyzed reduction of 2,6-diacetylpyridine (1) and produce more of the diol (2) with the same configuration in an enantiomerically enriched form. The two carbonyl functionalities of (1) are reduced in 90% conversion to produce the enantio-enriched C2-symmetric diol (40% ee, 47% de) using zinc trifluoromethanesulfonate and a catalytic amount of the chiral C 2-symmetric diol (2).

A Straightforward Deracemization of sec-Alcohols Combining Organocatalytic Oxidation and Biocatalytic Reduction

An efficient organocatalytic oxidation of racemic secondary alcohols, mediated by sodium hypochlorite (NaOCl) and 2-azaadamantane N-oxyl (AZADO), has been conveniently coupled with a highly stereoselective bioreduction of the intermediate ketone, catalyzed by ketoreductases, in aqueous medium. The potential of this one-pot two-step deracemization process has been proven by a large set of structurally different secondary alcohols. Reactions were carried out up to 100 mm final concentration enabling the preparation of enantiopure alcohols with very high isolated yields (up to 98 %). When the protocol was applied to the stereoisomeric rac/meso mixture of diols, these were obtained with very high enantiomeric excesses and diastereomeric ratios (95 % yield, >99 % ee, >99: 1 dr).

Highly enantioselective reduction of symmetrical diacetylaromatics with baker's yeast

Asymmetric reduction of symmetrical diacetylaromatics (1a, 1b, and 1d- g) with baker's yeast (Saccharomyces cerevisiae) provided the corresponding alcohols of high enantiomeric purity. By choosing appropriate reaction conditions, the products were preferentially the monoalcohols over the diols.

An efficient preparation of optically pure C2-symmetric aromatic diols by the asymmetric reduction of diacylaromatic compounds with B- chlorodiisopinocampheylborane

Asymmetric reduction of diacylaromatic compounds with B- chlorodiisopinocampheylborane provides the product diols in excellent diastereomeric and enantiomeric purity.