Synthesis of Protected Amino Hexitol Nucleosides as Building Blocks for Oligonucleotide Synthesis.
J Org Chem
; 83(24): 15155-15169, 2018 12 21.
Article
em En
| MEDLINE
| ID: mdl-30525618
ABSTRACT
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' â P6' phosphoramidates of amino hexitol nucleic acids (AHNA).
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1
Base de dados:
MEDLINE
Assunto principal:
Oligonucleotídeos
/
Álcoois Açúcares
Idioma:
En
Ano de publicação:
2018
Tipo de documento:
Article