ol026718w_si_002.pdf (63.87 kB)
A One-Pot Synthesis of β-C-Glucopyranosides from exo-Glucal, p-Tolylsulfenyl Chloride, an α-Methoxyalkene, and an External Nucleophile
journal contribution
posted on 2002-10-03, 00:00 authored by Hui Liu, Irina P. Smoliakova, Leonid N. Koikovβ-C-Glycosides were synthesized in one-pot experiments using the following sequence of four reactions: (i) addition of p-TolSCl to an
α-methoxyalkene, (ii) generation of the episulfonium ion from a β-(arylsulfanyl)alkyl chloride, (iii) reaction of the episulfonium intermediate
with benzylated exo-d-glucal to form a cyclic five-membered sulfonium salt, and (iv) quenching of the sulfonium salt with the external
nucleophile: H2O, CH3OH, or NaCNBH3.