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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.
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