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.
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