S. Manfredini, P. Baraldi, R. Bazzanini
Aug 1, 1994
Citations
0
Influential Citations
6
Citations
Journal
Tetrahedron Letters
Abstract
Abstract Tetrahydropyranyl (THP) derivatives of alcohols are converted in one-pot and in stereoselective manner into the corresponding 1- O -alkyl-2,3,5-tri- O -benzoyl-β-D-ribofuranosides on treatment with 1- O -acetyl-2,3,5-tri- O -benzoyl-β-D-ribofuranose and trimethylsilyl triflate (TMSOTf). The same protocol was also applyed on 1- O -acetyl-2,3,4,6-tetra- O -benzyl-glucopyranoside (α/β 9:1) to give, by reaction with 1- O -methyl-2,3,4-tri- O -benzyl-6-THP-α-D-glucopyranoside, the corresponding disaccaride (α/β 3:1). The reaction is high yielding and proceeds rapidly at very mild conditions (−30°C) on easily available starting materials.