Application of 516-12-1In 2020 ,《Synthesis of β-Glucosides with 3-O-Picoloyl-Protected Glycosyl Donors in the Presence of Excess Triflic Acid: A Mechanistic Study》 was published in Chemistry – A European Journal. The article was written by Mannino, Michael P.; Demchenko, Alexei V.. The article contains the following contents:
Our previous study showed that picoloylated donors are capable of providing excellent facial stereoselectivity through the H-bond-mediated aglycon delivery (HAD) pathway. Presented herein is a detailed mechanistic study of stereoselective glycosylation with 3-O-picoloylated glucosyl donors. While reactions of glycosyl donors equipped with the 3-O-benzoyl group are typically non-stereoselective because these reactions proceed via the oxacarbenium intermediate, 3-O-picoloylated donors are capable of providing enhanced, but somewhat relaxed, β-stereoselectivity by the HAD pathway. In an attempt to refine this reaction, we noticed that glycosylations are highly β-stereoselective in the presence of NIS and stoichiometric TfOH. The HAD pathway is highly unlikely because the picoloyl nitrogen is protonated under these reaction conditions. The protonation and glycosylation were studied by low-temperature NMR, and the intermediacy of the glycosyl triflate has been observed This article is dedicated to broadening the scope of this reaction in application to a variety of substrates and targets. After reading the article, we found that the author used 1-Iodopyrrolidine-2,5-dione(cas: 516-12-1Application of 516-12-1)
1-Iodopyrrolidine-2,5-dione(cas: 516-12-1) is used in the preparation of vinyl sulfones from olefins and benzenesulfinic acid. It acts as a source for I+ and involved in Hunsdiecker reactions for the conversion of cinnamic acids, and propiolic acids to the corresponding alfa-halostyrenes and 1-halo-1-alkynes respectively. Application of 516-12-1
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Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com