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Short Paper | Special issue | Vol 88, No. 2, 2014, pp.1587-1594
Published online, 30th September, 2013
DOI: 10.3987/COM-13-S(S)99
Glycosidation Reactions of Benzyl-Type Selenoglycoside Donors

Masanori Menjo, Hideki Tamai, Hiromune Ando,* Hideharu Ishida, Mamoru Koketsu, and Makoto Kiso*

*Faculty of Applied Biological Sciences, Gifu University , 1-1 Yanagido, Gifu, Gifu 501-1193, Japan


p-Methoxybenzyl (PMB), and p-nitrobenzyl (PNB) selenoglycosides of glucose were synthesized, and their glycosidation reactions were investigated. The Bn and PNB derivatives were successfully activated with IBr-AgClO4 to provide the glycosylated products in high yields. The glycosidation with the PMB derivatives required promotion with a metal triflate, such as (CuOTf)2·PhMe or In(OTf)3, and afforded the glycosylated products in medium to high yields.