445299-09-2Relevant academic research and scientific papers
New synthesis of 2,6-anhydro-β-D-fructofuranoses, pivotal [2.2.1] bicyclic acetals for the conversion of D-fructose into 2,2,5-trisubstituted tetrahydrofurans
Goursaud, Fabrice,Peyrane, Frédéric,Veyrières, Alain
, p. 3629 - 3637 (2007/10/03)
2,6-Anhydro-β-D-fructofuranose derivatives were prepared by a novel tin-promoted 2,5-cyclisation of phenyl 2-thio-β-D-fructopyranosides. They were regioselectively opened by allyltrimethylsilane in the presence of catalytic Sc(OTf)3 to give 2,2,5-trisubstituted tetrahydrofurans in high yields and major α-stereoselectivity.
