2′-O-(tert-Butyldimethylsilyl)-5′-O-trityluridine (CAS 117136-35-3)

2′-O-(tert-Butyldimethylsilyl)-5′-O-trityluridine is a chemically modified nucleoside that plays a significant role in the field of synthetic organic chemistry, particularly in the synthesis and study of nucleic acids. This compound is a derivative of uridine, where specific hydroxyl groups are protected to prevent unwanted side reactions during subsequent synthetic steps. In this molecule, the 2′-hydroxyl group is protected by a tert-butyldimethylsilyl (TBDMS) group, and the 5′-hydroxyl group is protected by a trityl group. These protecting groups are crucial because they make the molecule more stable and reactive under controlled conditions, facilitating the synthesis of more complex nucleic acid structures. The 2′-O-(tert-Butyldimethylsilyl) group is particularly important because it stabilizes the 2′-position against nucleophilic attack and prevents unwanted changes during various chemical reactions. This protection is essential when modifying the ribose sugar in RNA synthesis, as it allows chemists to selectively modify other parts of the nucleoside without altering the 2′-position. The 5′-O-trityl group serves a similar protective function but at the 5′-hydroxyl end. It is a common protecting group in nucleoside chemistry because it can be removed under mildly acidic conditions without disturbing other sensitive groups within the molecule. This selective deprotection is vital for linking nucleosides together to form oligonucleotides.