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First protection-free protocol for synthesis of 1-deoxy sugars through glycosyl dithiocarbamate intermediates
Authors:Gefei Li  Masato Noguchi  Kensuke Nakamura  Ryohei Hayasaka  Yuuki Tanaka  Shin-ichiro Shoda
Institution:Department of Biomolecular Engineering, Graduate School of Engineering, Tohoku University, 6-6-11-514, Aoba, Aoba-ku, Sendai 980-8579, Japan
Abstract:A practical two-step synthetic process for 1-deoxy sugars has been established. The process consists of the direct introduction of a dimethyldithiocarbamate group into the anomeric center of unprotected sugars and subsequent hydrogenation in the AIBN-H3PO2-NaHCO3 system. No protecting groups are needed to synthesize 1-deoxy monosaccharides and 1-deoxy disaccharides.
Keywords:1-Deoxy sugar  Glycosyl dithiocarbamate  Protection-free synthesis  Direct anomeric activation  Radical desulfurization
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