Takashi Seto

β-glucosyl esters of 19α-hydroxyursolic acid derivatives in leaves of Rubus species

Abstract β-Glucosyl esters of A-ring oxygenated 19α-hydroxyursolic acids were isolated from the leaves of Rubus microphyllus, R. koehneanus, R. trifidus and R. medius. Comparisons of the glycoside fractions of the leaves of 39 Rubus species were conducted, indicating the chemotaxonomic significance of this type of glucosyl ester in this genus.

AN EFFICIENT SYNTHESIS OF SULFO LEWIS X ANALOG CONTAINING 1-DEOXYNOJIRIMYCIN

Abstract Sulfo Lewisx analog containing 1-deoxynojirimycin (13) has been efficiently synthesized. Glycosidation of ethyl 2,3,4-tri-O-benzyl-1-thio-β-D-fucopyranoside (5) with O-2,6-di-O-benzoyl-3,4-isopropylidene-β-D-galactopyranosyl)-(1→4)-2,6-di-O-benzoyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-D-glucitol (4), prepared from O-β-D-galactopyranosyl-(1→4)-1,5-dideoxy-1,5-imino-D-glucitol (1) via 3 steps, and subsequent acid hydrolysis of the isopropylidene group gave the desired trisaccharide diol derivative (7) in good yield. Compound 7 was easily converted into 3′-O-sulfo Lewisx analog (13) via 6 steps in high yield. 1. Dedicated to the memory of Professor Akira Hasegawa.