82742-16-3Relevant articles and documents
Synthesis of fluorinated thiodigalactoside analogues
St-Gelais, Jacob,Leclerc, Christina,Giguère, Denis
, (2021/11/30)
In this work, we report the first synthesis of fluorinated thiodigalactoside analogues. We used tri-isopropylsilyl thioglycosides as masked glycosyl thiol nucleophiles for the elaboration of two monofluorinated heterodimers, one difluorinated homodimer, and one difluorinated heterodimer. Moreover, we also present an alternative synthesis of 3-deoxy-3-fluorogalactose and 4-deoxy-4-fluorogalactose from a common precursor. Finally, this small set of more stable thiodigalactoside analogues could be interesting inhibitors of galactose-specific lectins.
Reactions of 2-hydroxy-6,8-dioxabicyclo[3.2.1]oct-3-ene with diethylaminosulfur trifluoride and with halogens. Facile synthesis of 1,6- anhydrohalohexopyranoses
Oberdorfer, Franz,Haeckel, Roland,Lauer, Gilbert
, p. 201 - 206 (2007/10/03)
D-Galactal 1 reacts in THF in the presence of catalytic amounts of concentrated sulfuric acid to give (2R)-2-hydroxy-6,8-dioxabicyclo[3.2.1]oct- 3-ene (4) in a Ferrier-type rearrangement in 40% yield. When 4 is treated with diethylaminosulfur trifluoride