A Domino Epoxide Ring-Opening Xanthate Migration Reaction: An Alternative Entry to Thiosugars

COMBA, M. B.; MANGIONE, M.I.; SUÁREZ, A.G.; SAROTTI, A.M.; SPANEVELLO, R.A.*

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

WILEY-V C H VERLAG GMBH

Lugar: Weinheim; Año: 2018 p. 6848 - 6856

1434-193X

A sterereospecific and efficient synthesis of thiosugars derived from levoglucosenone and methyl α-D-glucopyranoside was developed by a domino epoxide ring openingxanthate migration to afford 1,3-oxathiolane-2-thiones in highyields. The stereochemical outcome of the new C?S bond was defined by the configuration of the starting materials. The 1,3-oxathiolane-2-thiones were subsequently submitted to a second tandem reaction affording the corresponding 2,3-episulfide alcohols. The thiosugars obtained are useful building blocks for the synthesis of thiooligosaccharides with potential biologicalproperties.