The tert-Butyldimethylsilyl Group as a Protecting Group in Deoxynucleosides

tert-Butyldimethylsilyl chloride reacts selectively with hydroxyl groups in nucleosides and preferentially with the 5′-hydroxyl of deoxynucleosides. The tert-butyldimethylsilyl group can be removed under conditions which do not affect other commonly used acid or base labile protecting groups, yet it is stable to phosphorylation conditions. This allows for the synthesis of a variety of protected deoxynucleosides in good yields and introduces a versatile new protecting group to the nucleoside and nucleotide field.