26922-79-2Relevant academic research and scientific papers
A Domino Epoxide Ring-Opening Xanthate Migration Reaction: An Alternative Entry to Thiosugars
Comba, María B.,Mangione, María I.,Suárez, Alejandra G.,Sarotti, Ariel M.,Spanevello, Rolando A.
, p. 6848 - 6856 (2018/12/11)
A sterereospecific and efficient synthesis of thiosugars derived from levoglucosenone and methyl α-d-glucopyranoside was developed by a domino epoxide ring opening- xanthate migration to afford 1,3-oxathiolane-2-thiones in high yields. 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 biological properties.
