Chemical Glycosylation with <i>p</i>-Methoxyphenyl (PMP) Glycosides via Oxidative Activation
Hyun Su Kim, Eunbin Jang, Hoe In Kim, Madala Hari Babu, Jae‐Young Lee, Sang Kyum Kim, Jaehoon Sim
Abstract
A novel persulfate-mediated oxidative glycosylation system using p -methoxyphenyl (PMP) glycosides as bench-stable glycosyl donors is developed. This study shows that both K 2 S 2 O 8 as an oxidant and Hf(OTf) 4 as a Lewis acid catalyst play important roles in the oxidative activation of the PMP group into a potential leaving group. This convenient glycosylation protocol proceeds under mild conditions and delivers a wide range of biologically and synthetically valuable glycoconjugates, including glycosyl fluorides.
Topics & Concepts
ChemistryGlycosylationGlycosylGlycoconjugateGlycosidePersulfateOxidative phosphorylationGlycosidic bondSulfationCombinatorial chemistryCatalysisGlycosyl donorOrganic chemistryBiochemistryEnzymeCarbohydrate Chemistry and SynthesisSulfur-Based Synthesis TechniquesChemical Synthesis and Reactions