Synthesis of Protected Amino Hexitol Nucleosides as Building Blocks for Oligonucleotide Synthesis
| Autor: | Amit M. Jabgunde, Piet Herdewijn, Swarup De, Leonid Beigelman, Rahul S. Patil, Steven De Jonghe |
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| Rok vydání: | 2018 |
| Předmět: |
Science & Technology
010405 organic chemistry Chemistry Organic Chemistry Oligonucleotides Chemistry Organic Stereoisomerism Chemistry Techniques Synthetic Oligonucleotide synthesis 010402 general chemistry 01 natural sciences Combinatorial chemistry THERAPIES 0104 chemical sciences Sugar Alcohols Physical Sciences Epoxy Compounds lipids (amino acids peptides and proteins) NUCLEIC-ACIDS D-ALTRITOL NUCLEOSIDES HYBRIDIZATION |
| Zdroj: | The Journal of Organic Chemistry. 83:15155-15169 |
| ISSN: | 1520-6904 0022-3263 |
| Popis: | A new synthesis protocol for the preparation of hitherto unknown 1',5'-anhydro-4'-amino-trityl/MMTr hexitol nucleosides has been developed. Key steps in the synthesis of the pyrimidine analogues (U and C) include the regioselective d- allo-hexitol oxirane and 2',4'-anhydronucleoside ring opening by uracil and azide, respectively. A different strategy using a regioselective epoxide ring opening of d- gulo-oxirane, followed by a SN2 type of azidation reaction, has been adopted for the purine analogues (A and G). These compounds can be easily converted to 6'-phosphoramidites for the solid-phase synthesis of N4' → P6' phosphoramidates of amino hexitol nucleic acids (AHNA). ispartof: JOURNAL OF ORGANIC CHEMISTRY vol:83 issue:24 pages:15155-15169 ispartof: location:United States status: published |
| Databáze: | OpenAIRE |
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