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.
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.
Capozzi
Giuseppe
G
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.
Catelani
Giorgio
G
D'Andrea
Felicia
F
Menichetti
Stefano
S
Nativi
Cristina
C
D002236:Carbohydrate Conformation; D006601:Hexoses / Q000737:chemistry*; D013013:Sorbose / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013865:Thioglycosides / Q000138:chemical synthesis
D006601:Hexoses; D013865:Thioglycosides; D013013:Sorbose