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Short Paper | Special issue | Vol 84, No. 2, 2012, pp.1335-1343
Published online, 3rd August, 2011
DOI: 10.3987/COM-11-S(P)69
A Synthetic Approach to Aromatic Aminoglycoside as a Neamine Mimic

Ryo Inoue, Sho Matsuda, Yoshiki Oda, Hirofumi Ooyama, Akihiro Yoshida, Keita Hamasaki, and Takashi Yamanoi*

*The Noguchi Institute, 1-8-1, Kaga, Itabashi-ku, Tokyo 173-0003, Japan

Abstract

This paper describes the synthetic approach to an aromatic α-glycoside as a mimic of neamine, which is a common core structure of some aminoglycoside antibiotics. We achieved the synthesis of the protected precursor of the neamine mimic, 4-(2,6-diamino-2,6-dideoxy-α-D-glucopyranosyloxy)-1,3-phenylenediamine, from N-acetyl-D-glucosamine and 2,4-diaminophenol as the starting materials using a glycosylation technique.