5'-O-(2-Isopropoxyprop-2-yl)-protected Phosphoramidite Building Blocks in the Liquid Phase Oligonucleotide Synthesis




Liang Zehong, Rosenqvist Petja, Pajuniemi Ella, Ora Mikko, Heinonen Petri, Virta Pasi, Oivanen Mikko

PublisherWILEY-V C H VERLAG GMBH

2023

European Journal of Organic Chemistry

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

EUR J ORG CHEM

e202300614

6

1434-193X

1099-0690

DOIhttps://doi.org/10.1002/ejoc.202300614(external)

https://doi.org/10.1002/ejoc.202300614(external)

https://research.utu.fi/converis/portal/detail/Publication/180811837(external)



5'-O-(2-isopropoxyprop-2-yl) (IIP)-protection was introduced to 5’-OH function of nucleosides in high yields by an acid-catalysed transacetalization with 2,2-diisopropoxypropane. The applicability of this temporal 5’-O-protecting group was demonstrated in the liquid phase oligonucleotide synthesis (LPOS) using the corresponding phosphoramidite building blocks (dA, dG, dC and dT) and a tetrapodal precipitative soluble support. Standard protecting groups were used on nucleobases. Tetrazole as an activator, followed by oxidation using m-chloroperbenzoic acid, was used for the coupling. The IIP was shown to be a capable choice to the 5’-O protection in solution phase synthesis. It could be readily removed with formic acid (t1/2<10 s in 6 % HCOOH in dichloromethane/methanol (2/1) at RT), resulting in volatile byproducts (acetone and isopropanol).


Last updated on 2024-26-11 at 23:41