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Note | Regular issue | Vol 75, No. 5, 2008, pp.1213-1223
Published online, 5th February, 2008
DOI: 10.3987/COM-07-11289
Applicability of Methyl 2,3,4-Tri-O-benzoyl-1-methanesulfonyl-α-D-glucopyranuronate as a Novel Quaternary Glucuronyl Reagent for Tertiary Amines

Ichiro Araya* and Hiroyuki Akita

*Reseach Center, Kyorin Pharmaceutical Co., Ltd., 1848 Nogi, Nogi-mcahi, Shimotsuga-gun, Tochigi, 329-0114, Japan

Abstract

Applicability of a methyl 2,3,4-tri-O-benzoyl-1-methanesulfonyl-α-D-glucopyranuronate 3 as a novel quaternary glucuronyl reagent was investigated. The reaction of 3 with an aromatic tertiary amines such as pyridine derivatives or imidazole derivatives proceeded to give quaternary N-glucuronides in a moderate yields, but the reaction of 3 with an aliphatic tertiary amine did not occur. In case of the reaction of 3 with nicotine which has aromatic and aliphatic tertiary amines in the molecule, the reaction proceeded selectively on the pyridine ring to give the corresponding N-glucuronide. The present reagent was considered to be useful for the formation of N-quaternary glucuronide from aromatic tertiary amines.