title: Conformational evaluation of some 4-deoxyhex-4-enopyranose derivatives and their use in the preparation of a previously undescribed class of 3-thio-L-sorbopyranosides and their 6-C-methoxy analogues.
abstract: A new series of thio-substituted sugars were synthesised relying on the totally regio- and stereoselective cycloaddition of 4-deoxyhex-4-enopyranose derivatives to 'in situ' generated oxothiones. Conformational studies of the above unsaturated sugars showed a marked prevalence of the all-axial conformer.
authors.affiliation: Centro CNR Chimica e Struttura Composti Eterociclici, Dipartimento di Chimica Organica Ugo Schiff, Universita' di Firenze, via della Lastruccia, 13 I-50019 Sesto Fiorentino (FI), Italy.
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Capozzi
authors.forename: Giorgio
authors.initials: G
authors.lastname: Catelani
authors.forename: Felicia
authors.initials: F
authors.lastname: D'Andrea
authors.forename: Stefano
authors.initials: S
authors.lastname: Menichetti
authors.forename: Cristina
authors.initials: C
authors.lastname: Nativi
mesh_terms: D002236:Carbohydrate Conformation; D006601:Hexoses / Q000737:chemistry*; D013013:Sorbose / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013865:Thioglycosides / Q000138:chemical synthesis
chemical_list: D006601:Hexoses; D013865:Thioglycosides; D013013:Sorbose