2′-O-(TBDMS)-3′-O-(phenoxythioncarbonyl)-5′-O-trityluridine (CAS 130860-11-6)

2′-O-(TBDMS)-3′-O-(phenoxythioncarbonyl)-5′-O-trityluridine is a chemically modified uridine derivative extensively used in nucleoside chemistry, particularly in the synthesis of complex RNA molecules. This compound features several protective groups: a tert-butyldimethylsilyl (TBDMS) group on the 2′ hydroxyl, a phenoxythioncarbonyl group on the 3′ hydroxyl, and a trityl group on the 5′ hydroxyl. These modifications are essential for stepwise synthesis processes where selective deprotection and functionalization are required. The presence of the TBDMS group at the 2′-hydroxyl position is crucial because it makes the molecule more stable under various conditions, allowing for selective reactions at other sites without interference. The TBDMS group can be removed under specific, mild acidic conditions, enabling further synthetic modifications while protecting the integrity of the ribose ring. The 3′-O-(phenoxythioncarbonyl) group is particularly interesting due to its role in facilitating nucleophilic attacks. This group can be used to introduce various nucleophiles at the 3′ position, a key step in constructing nucleotide linkages in RNA synthesis. This functionality is valuable for forming phosphodiester bonds that are essential for linking nucleotides together. On the other hand, the 5′-O-trityl group is a common protective group that provides stability and is easily removable under mildly acidic conditions without disturbing other sensitive functionalities. This selectivity is particularly useful in automated and manual oligonucleotide synthesis, where precise control over the introduction and removal of protecting groups is necessary.