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Review | Special issue | Vol 79, No. 1, 2009, pp.163-194
Published online, 12th December, 2008
DOI: 10.3987/REV-08-SR(D)4
Reactions and Uses of Artificial Ketoses

Takashi Yamanoi* and Sho Matsuda

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

Abstract

Some artificial ketoses having a naturally occurring aldose backbone can be readily prepared by the addition of RLi or RMgX to aldonolactone derivatives. They are expected to be a novel class of carbohydrate reagents for synthesizing valuable compounds. In order to utilize these ketoses completely, we must elucidate the reaction characteristics influenced by the ketose’s specific structures. In particular, it is important to understand the reaction specificities of the nucleophilic substitutions at the anomeric carbons of these ketoses to produce various ketosides. This review describes the nucleophilic reactions to form the ketosidic linkages from the artificial ketoses, focusing mainly on our recent research results.