Simultaneous regioselective protection of phenyl 1-thioglucosides at the C-3 and C-6 or at the C-2 and C-6 hydroxy groups

Simultaneous regioselective 3,6- or 2,6-selective protection of 1-thio-β- or α-d-glucopyranosides is described. The C-3 and C-6 hydroxy groups of the β-thioglucoside were selectively protected with triisopropylsilyl or tert-butyldiphenylsilyl trifluoromethanesulfonate. The C-2 and C-6 hydroxy groups of the α-thioglucoside were selectively protected with tert-butyldiphenylsilyl trifluoromethanesulfonate.