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

REPETTO, E.; MARINO, C; UHRIG, M. L.; VARELA, O.

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

Wiley-VCH, Verlag GmH and Co, KGaA

Lugar: Weinheim, Alemania; Año: 2008 vol. 2008 p. 540 - 547

1434-193X

Thiodisaccharides having a 1-thiopentofuranose nonreducing 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, by Michael addition, the thioglycosidic linkage. Alternatively, the MoO2Cl2-promoted glycosylation of the thiol group of 6-thiosugar derivatives by per-O-acylfuranose led to thiodisaccharides with exclusive 1,2-trans diastereocontrol.