ピラノース環酸素を硫黄原子で置換したチオオリゴサッカリドの合成研究

抄録

This paper describes the synthetic studies of sulfur substituted oligosaccharides performed in our laboratory. Efficient and α-selective glycosidation reactions with 5-thiopyranoses were realized employing 1-O-trichloroacetimidates of 5-thiopyranoses carrying 2-OΟ-etheral protective groups. These conditions were applied for the synthesis of sulfur substituted maltose and isothiomaltose derivatives. The Pummerer rearrangement of 2, 3-O-isopropylidene protected 1-dehydrothiopyranose oxide was found to proceed at the C 1 position regioselectively to provide 5-thiopyranose derivative. Experiments employing labeled compound revealed the reaction mechanism. Development of 3-cyano-3-tert-butyldimethylsilyl-propyl (CSP group) thioether brought us an successful synthesis of sulfur substituted galacturonic acid. Enzymatic properties of these analogue against endo-glycosidases are also described.