Mukherji, Ananya; Addanki, Rupa Bai; Halder, Suvendu; Kancharla, Pavan K. published their research in Journal of Organic Chemistry on December 3 ,2021. The article was titled 《Sterically Strained Bronsted Pair Catalysis by Bulky Pyridinium Salts: Direct Stereoselective Synthesis of 2-Deoxy and 2,6-Dideoxy-β-thioglycosides from Glycals》.Application of 20880-92-6 The article contains the following contents:
A sterically strained ionic Bronsted pair complex obtained from a sterically bulky base 2,4,6-tri-tert-butylpyridine and hydrochloric acid unusual reactivity to the anionic chloride. The complete shielding of the cationic [N-H]+ by the bulky ortho-tert-Bu groups weakens the possible hydrogen-bonding interactions with the chloride anion, and the [N-H]+···Cl- distance is unusually longer (3.10 Å). This results in strained/frustrated electrostatic interactions between the ion-pair, thus infusing an increased reactivity in both of the ions, which results in the activation of a third mol. like thiol via hydrogen-bonding. This intriguing weak interaction-based reactivity has been utilized to develop an organocatalytic synthesis of 2-deoxy-β-thioglycosides from glycals. While the 1H NMR studies showcase the diamagnetic activation of thiols in the presence of the catalyst, the ESR (EPR) studies reveal the generation of a radical species that suggests a possible frustrated radical pair catalysis. Besides, IR spectroscopic studies explain the intriguing influence of size/charge d. of the anion on the solvation-insusceptible, cationic [TTBPyH]+ and on the observed reactivity. In the experiment, the researchers used many compounds, for example, ((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol(cas: 20880-92-6Application of 20880-92-6)
((3aS,5aR,8aR,8bS)-2,2,7,7-Tetramethyltetrahydro-3aH-bis([1,3]dioxolo)[4,5-b:4′,5′-d]pyran-3a-yl)methanol(cas: 20880-92-6) is a useful reactant for examining the effectiveness of sulfamate and sulfamide groups for the inhibition of carbonic anhydrase-II (CA-II). And it is used as chiral auxiliaries in Michael and Aldol addition reactions.Application of 20880-92-6
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