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Review | Regular issue | Vol 78, No. 1, 2009, pp.19-44
Published online, 11th September, 2008
DOI: 10.3987/REV-08-638
Chemistry of 1-Methylenesugars: Synthetic Utilizations to 1’-C-Methyl-saccharides and Related Carbohydrates

Rie Namme and Shiro Ikegami*

*Faculty of Pharmaceutical Sciences, Teikyo University, 1091-1, Sagamiko, Kanagawa 299-0195, Japan

Abstract

The efficient synthesis of protected 1-methylenesugars and their acid-catalyzed O-glycosidation are mentioned in connection with that of 1-C-methyl-pyranoses. Application of this process to synthesis of the pentasaccharide PI-88 analogue was accomplished in a protected form. Also the syntheses of trehalose analogues and ulsonic acid derivatives were successful in the similar process. 1,3-Dipolar cycloaddition with nitrones provides the new types of spiro-heterocycles combined with carbohydrates. The closely related methylene-carbohydrates also provide a novel synthetic process for cyclitols that are useful synthetic intermediates for voglibose and related drugs.