Tetraisopropyldisiloxane-1,3-diyl as a versatile protecting group for pentopyranosides

The protecting group tetraisopropyldisiloxane-1,3-yl has been investigated for simultaneous protection of two hydroxyls on pentopyranosides. Methyl α-d-xylopyranoside is protected in excellent regioselectivity and high yield to form the 2,3-protected xylopyranoside whereas methyl β-d-xylopyranoside gives the 3,4-protected product also with excellent regioselectivity.

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► A new protecting group strategy for pentopyranosides is investigated.
► Simultaneous protection of two hydroxyls of xylosides to form a cyclic protecting group.
► Different regioselectivity is dependent of anomeric configuration.