title: A practical access to glucose- and allose-based (5+5) 3-spiropseudonucleosides from a common intermediate.
abstract: A practical access to glucose-based and allose-based spirooxazolidinones is reported. The synthetic sequence consisting of TEMPO-catalyzed oxidation of 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose, Henry reaction, and reduction provides amino alcohol with allo-configuration on a multigram scale. Alternatively, water elimination from Henry products followed by a rehydration gives an access to diastereomerically pure glucose-based nitro alcohol which upon reduction provides complementary amino alcohol with gluco-configuration. The latter amino alcohols are transformed into spirooxazolidinones (3-spiropseudonucleosides) via their N-Cbz or N-phenylcarbamate derivatives. The title compounds easily undergo N-derivatization and give highly crystalline materials. Two of the newly obtained (5+5) 3-spiropseudonucleosides are characterized by X-ray crystallography.
authors.affiliation: Faculty of Material Science and Applied Chemistry, Riga Technical University, Riga, Latvia. maris_turks@ktf.rtu.lv
authors.forename: Māris
authors.initials: M
authors.lastname: Turks
authors.forename: Vitalijs
authors.initials: V
authors.lastname: Rodins
authors.forename: Evija
authors.initials: E
authors.lastname: Rolava
authors.forename: Pāvels
authors.initials: P
authors.lastname: Ostrovskis
authors.forename: Sergey
authors.initials: S
authors.lastname: Belyakov
mesh_terms: D018360:Crystallography, X-Ray; D005947:Glucose / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D023303:Oxazolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D023303:Oxazolidinones; D013141:Spiro Compounds; C002055:allose; D005947:Glucose