2',3'-o-isopropylidene uridine

Description

2',3'-O-Isopropylidene uridine (2',3'-O-IPU) is a protected derivative of uridine, a nucleoside found in RNA. It is a valuable synthetic intermediate in the preparation of various modified nucleosides, which are used in the synthesis of therapeutic oligonucleotides. The isopropylidene group protects the 2' and 3' hydroxyl groups of uridine, preventing unwanted reactions at these positions. The synthesis of 2',3'-O-IPU typically involves reacting uridine with acetone in the presence of an acid catalyst. This reaction forms a cyclic ketal, protecting the 2' and 3' hydroxyl groups. The isopropylidene group can be removed under mild acidic conditions, regenerating the free hydroxyl groups. 2',3'-O-IPU has been used as a starting material for the synthesis of various modified nucleosides, such as 5-fluorouridine, 5-iodouridine, and 5-bromouridine. These modified nucleosides have been investigated for their therapeutic potential in treating various diseases, including cancer and viral infections. 2',3'-O-IPU is also an important building block for the synthesis of oligonucleotides, which are short sequences of nucleotides that can be used for various applications, such as gene therapy and diagnostics. The importance of studying 2',3'-O-IPU lies in its utility as a synthetic intermediate in the preparation of various modified nucleosides and oligonucleotides. Understanding the chemistry and reactivity of this compound is crucial for developing new and improved therapeutic agents and diagnostic tools. 2',3'-O-IPU has been used in various research studies investigating the synthesis, properties, and applications of modified nucleosides and oligonucleotides. These studies have led to the development of new therapeutic agents and diagnostic tools that have improved patient outcomes.'

2',3'-O-isopropylidene uridine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]