The synthesis of hitherto unknown 1-[3-(hydroxymethyl)-2- methyl-4-methyleneisoxazolidin-5-yl]thymine (5), 1-{(Z)-[3- (hydroxymethyl)-2-methylisoxazolidin-4-ylidene]methyl}- thymine (6), and 1-{(E)-[3-(hydroxymethyl)-2-methylisoxazolidin- 5-ylidene]methyl}thymine (7) is described. The first compound can be regarded as a N,O-analogue of Entecavir and DMDC, which contains thymine as a nucleobase. The key allenic nucleobase was prepared in good yields starting from 2,3-dibromopropene. The subsequent 1,3-dipolar cycloaddition proceeded with good site selectivity to give 5 and regioisomeric nucleosides 6 and 7.

A novel class of modified nucleosides: synthesis of alkylidene isoxazolidinyl nucleosides containing thymine

PIPERNO, Anna;ROMEO, Roberto
2007

Abstract

The synthesis of hitherto unknown 1-[3-(hydroxymethyl)-2- methyl-4-methyleneisoxazolidin-5-yl]thymine (5), 1-{(Z)-[3- (hydroxymethyl)-2-methylisoxazolidin-4-ylidene]methyl}- thymine (6), and 1-{(E)-[3-(hydroxymethyl)-2-methylisoxazolidin- 5-ylidene]methyl}thymine (7) is described. The first compound can be regarded as a N,O-analogue of Entecavir and DMDC, which contains thymine as a nucleobase. The key allenic nucleobase was prepared in good yields starting from 2,3-dibromopropene. The subsequent 1,3-dipolar cycloaddition proceeded with good site selectivity to give 5 and regioisomeric nucleosides 6 and 7.
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11570/1717784
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