308366-26-9

Usage

Chirality

Chiral molecule

Stereocenter

Single stereocenter (1R)

Enantiomers

Exists in two mirror-image forms

Applications

a. Building block or intermediate in the synthesis of pharmaceuticals
b. Used in the synthesis of other organic compounds
c. Potential applications in medicinal chemistry and drug discovery

Handling considerations

Requires careful handling to avoid enantiomeric contamination

Upstream product

• 89791-91-3 2-hydroxy-2-(pyridin-2-yl)acetic acid 
• 100-69-6 2-vinylpyridine 
• 55967-94-7 2-oxiranylpyridine 
• 162085-26-9 (S)-4-(2-pyridyl)-2,2-dimethyl-1,3-dioxolane 

Downstream Products

• 95836-52-5 2-(α-hydroxyacetyl)pyridine 
• 160821-26-1 (R)-2-(1-amino-2-hydroxyethyl)pyridine 

Relevant academic research and scientific papers

2-Acetylpyridine thiosemicarbazones XI: 2-(α-hydroxyacetyl)pyridine thiosemicarbazones as antimalarial and antibacterial agents

A series of 2-(α-hydroxyacetyl)pyridine thiosemicarbazones was synthesized as potential antimalarial and antibacterial agents. Their synthesis was achieved by the condensation of N4-mono- or N4,N4-disubstituted thiosemicarbazides with 2-(α-hydroxyacetyl)pyridine. The latter was prepared by selective bromide oxidation of (2-pyridinyl)-1,2-ethanediol. The new compounds show potent inhibitory activity against penicillin-sensitive as well as penicillin-resistant Neisseria gonorrhoeae (MIC, 0.5-0.004 μg/mL), against Neisseria meningitidis (MIC, 0.5-0.032 μg/mL), and Staphylococcus aureus (MIC, 0.5-2 μg/mL). Good in vitro antimalarial effects against Plasmodium falciparum (Smith strain; ID50, 6.7-38 ng/mL) were observed in most of these new agents, but only 3 of 12 compounds exhibit moderate in vivo activity against Plasmodium berghei. These new agents appear to be less toxic to the host and more water soluble than the corresponding 2-acetylpyridine thiosemicarbazones.

Iodine-Initiated Dioxygenation of Aryl Alkenes Using tert-Butylhydroperoxides and Water: A Route to Vicinal Diols and Bisperoxides

An environment-friendly and efficient dioxygenation of aryl alkenes for the construction of vicinal diols has been developed in water with iodine as the catalyst and tert-butylhydroperoxides (TBHPs) as the oxidant. The protocol was efficient, sustainable, and operationally simple. Detailed mechanistic studies indicated that one of the hydroxyl groups is derived from water and the other one is derived from TBHP. Additionally, the bisperoxides could be obtained in good yields with iodine as the catalyst, Na2CO3 as the additive, and propylene carbonate as the solvent, instead.

Total synthesis of hibispeptin A via Pd-catalyzed C(sp3)-H arylation with sterically hindered aryl iodides

To access the key Ile-Hpa pseudodipeptide motif in hibispeptins, a series of bidentate carboxamide-based auxiliary groups have been explored to facilitate the palladium-catalyzed arylation of unactivated γ-C(sp3)-H bonds of Ile precursor with a

Microbiological transformations. 47. A step toward a green chemistry preparation of enantiopure (S)-2-, -3-, and -4-pyridyloxirane via an epoxide hydrolase catalyzed kinetic resolution

The biocatalyzed hydrolytic kinetic resolution of 2-, 3-, and 4-pyridyloxirane by the Aspergillus niger epoxide hydrolase (EH) has been explored. This was used to perform a gram scale preparation of these epoxides of (S) absolute configuration using a process performed at a concentration as high as 10 g/L (82 mM). All three epoxides have been obtained in a nearly enantiopure form (ee > 98%). Interestingly, it was shown that this biotransformation could be achieved using plain water instead of buffer solution, an important improvement as far as downstream processing of an eventual industrial process is concerned. Neither of these substrates could be obtained in reasonable enantiomeric purity and yield using the nowadays most efficient metal-based catalysts.

Microbiological transformations. Part 48: Enantioselective biohydrolysis of 2-, 3- and 4-pyridyloxirane at high substrate concentration using the Agrobacterium radiobacter AD1 epoxide hydrolase and its Tyr215Phe mutant

The epoxide hydrolase (EH) from Agrobacterium radiobacter AD1 wild type (ArWT) and its Tyr215Phe mutant were compared for the biocatalyzed hydrolytic kinetic resolution (BHKR) of 2-, 3- and 4-pyridyloxirane. The regioselectivity of the oxirane ring opening as well as the substrate concentration limit and the inhibitory effect of the diol were determined. A gram scale preparation of enantiopure 2-pyridyloxirane (ee>98%) at a concentration as high as 127 mM (15.5 g/L) could be achieved with each of these two enzymes.

Microbiological transformations. Part 46: Preparation of enantiopure (S)-2-pyridyloxirane via epoxide hydrolase-catalysed kinetic resolution

The hydrolytic kinetic resolution (HKR) of 2-pyridyloxirane is described, using the overexpressed epoxide hydrolase from the filamentous fungus Aspergillus niger. This allows the preparation of the (S)-enantiomer of this product in enantiopure form (ee >9

Synthesis of Optically Active Hydroxyalkylpyridines and Related Pyridyl Amines

2-(1-Hydroxyalkyl)pyridines have been prepared by cobalt(I)-catalyzed cocyclotrimerization reaction of O-protected α-hydroxynitriles with acetylene.From these compounds the related pyridyl amines have been obtained.