UNIT 2.9 Preparation of 2′-O-[(Triisopropylsilyl)oxy]methyl-protected Ribonucleosides
Published Online: 1 FEB 2002
Copyright © 2003 by John Wiley and Sons, Inc.
Lab Protocol Title
Current Protocols in Nucleic Acid Chemistry
How to Cite
Pitsch, S. and Weiss, P. A. 2002. Preparation of 2′-O-[(Triisopropylsilyl)oxy]methyl-protected Ribonucleosides. Current Protocols in Nucleic Acid Chemistry. 7:2.9:2.9.1–2.9.14.
- Published Online: 1 FEB 2002
- Published Print: DEC 2001
The [(triisopropylsilyl)oxy]methyl (TOM) group is a useful protecting group for the 2′-OH of ribonucleosides to be used for oligoribonucleotide synthesis by the phosphoramidite method. It is completely stable to all reaction conditions applied during assembly and the first deprotection step. It does not interfere with the coupling reaction and leads to very good coupling yields under DNA-coupling conditions. The final cleavage occurs quantitatively without concomitant destruction of the RNA product. This unit describes the synthesis and characterization of 2′-O-TOM-5′-O-dimethoxytrityl-N-acetyl ribonucleosides in full detail. The TOM-group is introduced via a dibutyltin dichloride-mediated reaction into N-acetylated, 5′-O-dimethoxytritylated ribonucleosides. Support protocols describe the synthesis of N-acetylated, 5′-O-dimethoxytritylated adenosine and guanosine, as well as synthesis of the starting reagent [(triisopropylsilyl)oxy]methyl chloride (TOM-Cl). Preparation of the phosphoramidites and their use in solid-phase oligonucleotide synthesis are described elsewhere in the series.