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- W3200585324 abstract "N,N-Diacetylimido protection of 2-aminoglycosides is an elegant strategy but has had limited applications due to unexpected side reactions in glycosylation. We found that high acid concentrations could diminish the side reactions. We observed intermolecular hydrogen bonding among alcohols and acids could disrupt. Assuming that intermolecular hydrogen bonding accelerates the formation of 1,2-orthoamides and disrupting intermolecular hydrogen bonds could turn to the desired glycosylation, we successfully employed sulfenyl triflate pre-activation in the glycosylation of a broad scope of alcohol acceptors, as well as in a one-pot synthesis of a protected human milk oligosaccharide, lacto-N-neotetraose." @default.
- W3200585324 created "2021-09-27" @default.
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- W3200585324 date "2021-09-17" @default.
- W3200585324 modified "2023-10-17" @default.
- W3200585324 title "Reinvestigation of N,N-Diacetylimido-Protected 2-Aminothioglycosides in O-Glycosylation: Intermolecular Hydrogen Bonds Contributing to 1,2-Orthoamide Formation" @default.
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- W3200585324 doi "https://doi.org/10.1021/acs.joc.1c01009" @default.
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