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Paper | Special issue | Vol 84, No. 2, 2012, pp.1123-1140
Published online, 9th September, 2011
DOI: 10.3987/COM-11-S(P)94
Regioselective Glycosylation of Unprotected Methyl Hexopyranoside by Transient Masking with Arylboronic Acid

Takashi Nishino, Yohei Ohya, Rie Murai, Tatsuya Shirahata, Daisuke Yamamoto, Kazuishi Makino, and Eisuke Kaji*

*School of Pharmacy, Kitasato University, Shirokane 5-9-1, Minato-ku, Tokyo 108-8641, Japan

Abstract

Unprotected methyl α/β-D-galactopyranoside, α/β-D-glucopyranoside, α-L-fucopyranoside, and α-L-rhamnopyranoside were regioselectively glycosylated by treatment with per-O-pivaloyl-α-D-glycopyranosyl bromide to give glycosyl-β(1→3)-galactopyranoside, glycosyl- β(1→2/3)-glucopyranoside, glycosyl-β(1→2)-fucopyranoside, and glycosyl- β(1→4)-rhamnopyranoside, respectively. The reaction mainly occurred at the secondary hydroxy group, even in the presence of a primary hydroxy group, which was masked with arylboronic acid.