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Molecules 2009, 14(11), 4326-4336; doi:10.3390/molecules14114326

Towards the Synthesis of Inosine Building Blocks for the Preparation of Oligonucleotides with Hydrophobic Alkyl Chains Between the Nucleotide Units

Organische Materialchemie und Bioorganische Chemie, Institut für Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany
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Received: 18 September 2009 / Revised: 19 October 2009 / Accepted: 23 October 2009 / Published: 26 October 2009
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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.
Keywords: lipophilic oligonucleotides; phosphoramidites; nucleoside ketals lipophilic oligonucleotides; phosphoramidites; nucleoside ketals
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MDPI and ACS Style

Köstler, K.; Rosemeyer, H. Towards the Synthesis of Inosine Building Blocks for the Preparation of Oligonucleotides with Hydrophobic Alkyl Chains Between the Nucleotide Units. Molecules 2009, 14, 4326-4336.

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