Development of the systematic synthetic method of human pseudo-oligosaccharides which have the carbasugar at the nonreducing end

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Recently, the production of 2-deoxy-scyllo-inosose (DOI) was accomplished by the bioconversion using metabolically engineered E. coli. DOI which is cyclohexanone derivative having four OH groups is suitable as a precursor of carbasugars.First, 6-O-Ac-carba-beta-D-Glc was synthesized from DOI. Then, we attempted to the synthesis of carbasugars featuring the random pivaloylation of 6-O-Ac-carba-beta-D-Glc, by which partially protected products are obtained at a time. As the results, we accomplished the synthesis of 5a-carba-beta-D-Gal, 5a-carba-beta-D-Man, 5a-carba-beta-D-All and 5a-carba-beta-D-ManNAc by use of the partially protected products.Additionally, synthesis of 5a,5a'-dicarba-beta-D-isomaltose derivative (47%), 5a,5a'-dicarba-beta-D-maltose derivative (3%) and 5a,5a'-dicarba-alpha,beta-D-trehalose derivative (37%) were achieved by the coupling reaction between carba-beta-D-glucose donor and acceptor under high-concentration condition of substrates at 0 degrees Celsius.