Next Article in Journal
Forming Glasses from Se and Te
Previous Article in Journal
Synthesis and Characterization of Some Chiral Metal-Salen Complexes Bearing a Ferrocenophane Substituent
Molecules 2009, 14(11), 4326-4336; doi:10.3390/molecules14114326
Article

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

 and *
Organische Materialchemie und Bioorganische Chemie, Institut für Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany
* Author to whom correspondence should be addressed.
Received: 18 September 2009 / Revised: 19 October 2009 / Accepted: 23 October 2009 / Published: 26 October 2009
Download PDF [209 KB, uploaded 18 June 2014]   |  

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
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).
SciFeed

Share & Cite This Article

Further Mendeley | CiteULike
Export to BibTeX |
EndNote |
RIS
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.

View more citation formats

Related Articles

Article Metrics

For more information on the journal, click here

Comments

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert