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- Title
Towards the Synthesis of Inosine Building Blocks for the Preparation of Oligonucleotides with Hydrophobic Alkyl Chains Between the Nucleotide Units.
- Authors
Köstler, Karl; Rosemeyer, Helmut
- Abstract
The scientific objective of the research reported in this manuscript was the synthesis of novel phosphoramidite building blocks for the preparation of lipophilic oligonucleotides. Reaction of inosine (4) with 4-oxopentyl-4-methylbenzoate (2c) in the presence of triethyl orthoformate and 4M HCl in 1,4-dioxane gave a diastereoisomeric mixture of the ketals 5. Subsequent 4,4′-dimethoxytritylation at the 5′-hydroxyl afforded (R)-6 + (S)-6 which could be separated chromatographically. Detoluoylation gave compounds (R)-7 and (S)-7. Phosphitylation of a diastereoisomeric mixture of 7 led to a mixture of four diastereoisomers of the corresponding 2-cyanoethylphosphoramidites 8.
- Subjects
OLIGONUCLEOTIDES; NUCLEOSIDES; INOSINE; HYDROXYL group; GENE therapy; OLIGOMERS; DRUG lipophilicity; RNA; KETONES
- Publication
Molecules, 2009, Vol 14, Issue 11, p4326
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules14114326