Two straightforward strategies for the synthesis of thiodisaccharides with a furanose unit as nonreducing end

REPETTO, EVANGELINA; MARINO, CARLA; UHRIG, MARÍA LAURA; VARELA, OSCAR

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Wiley

Lugar: Weinheim; Año: 2008 p. 540 - 547

1434-193X

Thiodisaccharides having a 1-thiopentofuranose as non-reducing end were synthesized by two routes starting from per-O-acylaldofuranoses with arabino, ribo and xylo configurations. These glycosyl donors were converted into S-glycosyl isothiourea derivatives as precursors of 1-thiofuranose units, which were generated in situ and trapped by a sugar enone to produce, via Michael addition, the thioglycosidic linkage. Alternatively, the MoO2Cl2-promoted glycosylation of the thiol group of 6-thiosugar derivatives by per-O-acylfuranoses led to thiodisaccharides with exclusive 1,2-trans-diasterocontrol.