Towards the Synthesis of Inosine Building Blocks for the Preparation of Oligonucleotides with Hydrophobic Alkyl Chains Between the Nucleotide Units
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,...
| Main Authors: | , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2009-10-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/14/11/4326/ |
| _version_ | 1811249058370551808 |
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| author | Karl Köstler Helmut Rosemeyer |
| author_facet | Karl Köstler Helmut Rosemeyer |
| author_sort | Karl Köstler |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-04-12T15:39:51Z |
| format | Article |
| id | doaj.art-4de3f1f1ba9d429c990dc0906e490015 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-04-12T15:39:51Z |
| publishDate | 2009-10-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-4de3f1f1ba9d429c990dc0906e4900152022-12-22T03:26:49ZengMDPI AGMolecules1420-30492009-10-0114114326433610.3390/molecules14114326Towards the Synthesis of Inosine Building Blocks for the Preparation of Oligonucleotides with Hydrophobic Alkyl Chains Between the Nucleotide UnitsKarl KöstlerHelmut RosemeyerThe 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.http://www.mdpi.com/1420-3049/14/11/4326/lipophilic oligonucleotidesphosphoramiditesnucleoside ketals |
| spellingShingle | Karl Köstler Helmut Rosemeyer Towards the Synthesis of Inosine Building Blocks for the Preparation of Oligonucleotides with Hydrophobic Alkyl Chains Between the Nucleotide Units Molecules lipophilic oligonucleotides phosphoramidites nucleoside ketals |
| title | Towards the Synthesis of Inosine Building Blocks for the Preparation of Oligonucleotides with Hydrophobic Alkyl Chains Between the Nucleotide Units |
| title_full | Towards the Synthesis of Inosine Building Blocks for the Preparation of Oligonucleotides with Hydrophobic Alkyl Chains Between the Nucleotide Units |
| title_fullStr | Towards the Synthesis of Inosine Building Blocks for the Preparation of Oligonucleotides with Hydrophobic Alkyl Chains Between the Nucleotide Units |
| title_full_unstemmed | Towards the Synthesis of Inosine Building Blocks for the Preparation of Oligonucleotides with Hydrophobic Alkyl Chains Between the Nucleotide Units |
| title_short | Towards the Synthesis of Inosine Building Blocks for the Preparation of Oligonucleotides with Hydrophobic Alkyl Chains Between the Nucleotide Units |
| title_sort | towards the synthesis of inosine building blocks for the preparation of oligonucleotides with hydrophobic alkyl chains between the nucleotide units |
| topic | lipophilic oligonucleotides phosphoramidites nucleoside ketals |
| url | http://www.mdpi.com/1420-3049/14/11/4326/ |
| work_keys_str_mv | AT karlkostler towardsthesynthesisofinosinebuildingblocksforthepreparationofoligonucleotideswithhydrophobicalkylchainsbetweenthenucleotideunits AT helmutrosemeyer towardsthesynthesisofinosinebuildingblocksforthepreparationofoligonucleotideswithhydrophobicalkylchainsbetweenthenucleotideunits |