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

Autor(en): Koestler, Karl
Rosemeyer, Helmut 
Stichwörter: ACETALS; ADENOSINE-DEAMINASE; AFFINITY RESINS; Biochemistry & Molecular Biology; Chemistry; Chemistry, Multidisciplinary; DERIVATIVES; IMMOBILIZATION; lipophilic oligonucleotides; nucleoside ketals; phosphoramidites; SPACER
Erscheinungsdatum: 2009
Herausgeber: MDPI
Volumen: 14
Ausgabe: 11
Startseite: 4326
Seitenende: 4336
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.
ISSN: 14203049
DOI: 10.3390/molecules14114326

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