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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 *
Received: 18 September 2009; in revised form: 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.

AMA 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(11):4326-4336.

Chicago/Turabian Style

Köstler, Karl; Rosemeyer, Helmut. 2009. "Towards the Synthesis of Inosine Building Blocks for the Preparation of Oligonucleotides with Hydrophobic Alkyl Chains Between the Nucleotide Units." Molecules 14, no. 11: 4326-4336.


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