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Anomeric Thioglycosides Give Different Anomeric Product Distributions under NIS/TfOH Activation

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DOI

The reaction of a series of anomeric thioglycosides with various glycosyl acceptors and N-iodosuccinimide/catalytic triflic acid was investigated with respect to reactivity and anomeric selectivity. In general, β-configured donors were found to give a more β-selective reaction outcome compared to their α-configured counterparts. The relative reactivity of various thioglycosides was measured through competition experiments, and the following order was established: phenyl, tolyl, methyl, ethyl, isopropyl, and 1-adamantyl.

Original languageEnglish
JournalJournal of Organic Chemistry
Volume87
Issue6
Pages (from-to)4154-4167
Number of pages14
ISSN0022-3263
DOIs
Publication statusPublished - Mar 2022

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