title: Synthesis of a novel 1,2-dithianenucleoside via Pummerer-like reaction, followed by Vorbruggen glycosylation between a 1,2-dithiane derivative and uracil.
abstract: The novel 1,2-dithianenucleoside was designed as a hybrid type of modification between 4'-thioribonucleoside and altritol nucleoside. The desired compound, i.e., 1-[(3R,4R,5S,6R)-4,5-dihydroxy-6-hydroxymethyl-1,2-dithianyl]uracil (20), was prepared via the Pummerer-like reaction, followed by Vorbruggen glycosylation between an appropriately protected 1,2-dithiane derivative and silylated uracil.
authors.affiliation: Graduate School of Pharmaceutical Sciences, The University of Tokushima, Shomachi 1-78-1, Tokushima 770-8505, Japan.
authors.forename: Tadashi
authors.initials: T
authors.lastname: Miyazawa
authors.forename: Kouhei
authors.initials: K
authors.lastname: Umezaki
authors.forename: Noriko
authors.initials: N
authors.lastname: Tarashima
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Furukawa
authors.forename: Takashi
authors.initials: T
authors.lastname: Ooi
authors.forename: Noriaki
authors.initials: N
authors.lastname: Minakawa
mesh_terms: D018360:Crystallography, X-Ray; D006031:Glycosylation; D008968:Molecular Conformation; D011807:Quinolizines / Q000737:chemistry*; D013455:Sulfur / Q000737:chemistry; D013457:Sulfur Compounds / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis
chemical_list: D011807:Quinolizines; D013457:Sulfur Compounds; C438055:dithiane; D014498:Uracil; D013455:Sulfur