Kelemen, Viktor; Bege, Miklos; Eszenyi, Daniel; Debreczeni, Nora; Benyei, Attila; Stuerzer, Tobias; Herczegh, Pal; Borbas, Aniko published an article in 2019, the title of the article was Stereoselective Thioconjugation by Photoinduced Thiol-ene Coupling Reactions of Hexo- and Pentopyranosyl D- and L-Glycals at Low-Temperature-Reactivity and Stereoselectivity Study.Electric Literature of 2873-29-2 And the article contains the following content:
A comprehensive optimization and mechanistic study on the photoinduced hydrothiolation of different D- and L- hexo- and pentoglycals with various thiols was performed, at the temperature range of RT to -120 °C. Addition of thiols onto 2-substituted hexoglycals proceeded with complete 1,2-cis-α-stereoselectivity in all cases. Hydrothiolation of 2-substituted pentoglycals resulted in mixtures of 1,2-cis-α- and -β-thioglycosides of varying ratio depending on the configuration of the reactants. Hydrothiolation of unsubstituted glycals at -80 °C proceeded with excellent yields and, except for galactal, provided the axially C2-S-linked isomers with high selectivity. Cooling was always beneficial to the efficacy, increased the yields and in most cases significantly raised the stereoselectivity. The suggested mechanism explains the different conformational preferences of the intermediate carbon-centered radicals, which is a crucial factor in the stereoselectivity of the reactions. The experimental process involved the reaction of (2R,3S,4R)-2-(Acetoxymethyl)-3,4-dihydro-2H-pyran-3,4-diyl diacetate(cas: 2873-29-2).Electric Literature of 2873-29-2
The Article related to low temperature stereoselective photoinduced thiol ene coupling glycal thiol, glycal, photoactivation, stereoselective synthesis, thioglycoside, thiyl radical addition, Carbohydrates: Oligosaccharides and other aspects.Electric Literature of 2873-29-2
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