title: Stereospecific synthesis of aldoses based on the epoxide-opening reaction with double inversion of the configuration.
abstract: A new synthetic methodology for aldoses and aldonitols was developed in which two stereospecific epoxide-opening reactions with double inversion of the configuration, i.e., the ring-opening reaction of epoxy sulfides with phenylboronic acid and the stereospecific interconversion of trans- and cis-epoxy sulfides, were designed as the key steps. The synthetic potential of the new methodology was exemplified by the highly stereoselective synthesis of two pentose-derived sugars, arabitol and adonitol (ribitol).
authors.affiliation: Division of Chemistry, Graduate School of Science, Hokkaido University, Sapporo, Japan.
authors.forename: Atsushi
authors.initials: A
authors.lastname: Hirai
authors.forename: Terumichi
authors.initials: T
authors.lastname: Tonooka
authors.forename: Keiji
authors.initials: K
authors.lastname: Tanino
authors.forename: Masaaki
authors.initials: M
authors.lastname: Miyashita
mesh_terms: D002241:Carbohydrates / Q000138:chemical synthesis* / Q000737:chemistry; D004852:Epoxy Compounds; D007202:Indicators and Reagents; D008958:Models, Molecular; D008968:Molecular Conformation; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D002241:Carbohydrates; D004852:Epoxy Compounds; D007202:Indicators and Reagents