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• W2016070596 abstract "Structural modifications of the leaving group of S-glycosyl O-methyl phenylcarbamothioates (SNea) involving change of substituents that express different electronic effects led to a better understanding of how the reactivity of these glycosyl donors can be modified by changing the structure of their leaving groups. Mechanistic studies involving the isolation of departed aglycones were indicative of the direct activation of both p-methoxy-SNea and p-nitro-SNea leaving groups via the anomeric sulfur rather than the remote nitrogen atom. The presence of an electron donating substituent (p-methoxy) has a strong effect on the nucleophilicity of the sulfur atom that becomes more susceptible toward the attack of thiophilic reagents, in particular. This key observation allowed to differentiate the reactivity levels of p-methoxy-SNea versus p-nitro-SNea and even unmodified SNea leaving groups. The reactivity difference observed in the series of SNea leaving groups is sufficient to be exploited in expeditious oligosaccharide synthesis via selective activation strategies." @default.
• W2016070596 created "2016-06-24" @default.
• W2016070596 creator A5043089901 @default.
• W2016070596 creator A5051464035 @default.
• W2016070596 date "2015-02-01" @default.
• W2016070596 modified "2023-09-23" @default.
• W2016070596 title "Glycosyl alkoxythioimidates as building blocks for glycosylation: a reactivity study" @default.
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• W2016070596 doi "https://doi.org/10.1016/j.carres.2014.06.025" @default.
• W2016070596 hasPubMedId "https://pubmed.ncbi.nlm.nih.gov/25043398" @default.
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