53008-64-3Relevant academic research and scientific papers
Versatile Glycosyl Sulfonates in β-Selective C-Glycosylation
Bennett, Clay S.,Ling, Jesse
, p. 4304 - 4308 (2020)
C-Glycosides are both a common motif in many bioactive natural products and important glycoside mimetics. We demonstrate that activating a hemiacetal with a sulfonyl chloride, followed by treating the resultant glycosyl sulfonate with an enolate results i
Matching Glycosyl Donor Reactivity to Sulfonate Leaving Group Ability Permits SN2 Glycosylations
Zhuo, Ming-Hua,Wilbur, David J.,Kwan, Eugene E.,Bennett, Clay S.
supporting information, p. 16743 - 16754 (2019/10/16)
Here we demonstrate that highly β-selective glycosylation reactions can be achieved when the electronics of a sulfonyl chloride activator and the reactivity of a glycosyl donor hemiacetal are matched. While these reactions are compatible with the acid- and base-sensitive protecting groups that are commonly used in oligosaccharide synthesis, these protecting groups are not relied upon to control selectivity. Instead, β-selectivity arises from the stereoinversion of an α-glycosyl arylsulfonate in an SN2-like mechanism. Our mechanistic proposal is supported by NMR studies, kinetic isotope effect (KIE) measurements, and DFT calculations.
Sugar Tosylates via p-Toluenesulfinic Acid Esters. - p-Toluenesulfinimidazolide - A Reagent for Formation of Sulfinic Acid Esters without Using Halides
Redlich, Hartmut,Meyer, Wolf-Ulrich
, p. 1354 - 1360 (2007/10/02)
The reaction of the protected sugar derivatives 1, 4, 7, 10, 13, 16, 19 and 20 with p-toluenesulfinimidazolide prepared from p-toluenesulfinic acid and N,N'-carbonyldiimidazole yields the corresponding p-toluenesulfinic esters 2, 5, 8, 11, 14, 17, 20 and 22.With the exception of 20 and 22, these products can be oxidized with m-chloroperbenzoic acid in high yields and short overall reaction times to the tosylates 3, 6, 9, 12, 15 and 18.
