Abstract2′–5′ Adenylate trimers41–44carrying the (tert‐butyl)dimethylsilyl (tbds) group at the 3′‐OH position of various sugar moieties were synthesizedviathe phosphoramidite method. The use of the (tert‐butyloxy)carbonyl (boc) and 2‐(4‐nitrophenyl)ethylsulfonyl (npes) groups for 2′‐OH protection in neighbourhood to the 3′‐O‐tbds residue was compared during the synthesis of the target trimers. For other functional positions, the use of the 2‐(4‐nitrophenyl)ethyl (npe) and 2‐(4‐nitrophenyl)ethoxycarbonyl