The synthesis of some 5-substituted-6-aza-2'-deoxyuridines

Article abstract of DOI:10.1080/15257779408013233

5-(2-Thienyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)- 6-azauracil [VIII] and 5-cyclopropyl-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D- erythro-pentofuranosyl)-6-azauracil [X] were obtained in high yields (93.5% and 81.3% respectively) exclusively as β anomers, by condensation of the corresponding silylated triazine bases with 2-deoxy-3,5-di-O-p-toluoyl-D- erythro-pentosyl chloride in chloroform. After deblocking both nucleosides with sodium methoxide in methanol, 5-(2-thienyl)-6-aza-2'-deoxyuridine [IX] and 5-cyclopropyl-6-aza-2'-deoxyuridine [XI] were obtained. The nucleoside IX was further acetylated, brominated with Br₂/CCl₄ and deblocked with methanolic ammonia to give 6-aza-5[2-(5-bromothienyl)]-2'-deoxyuridine [XIV].

Full text of DOI:10.1080/15257779408013233

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Nucleosides and Nucleotides
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The Synthesis of Some 5-Substituted-6-
aza-2′-deoxyuridines
I. Basnak a , P. L. Coe a & R. T. Walker a
a School of Chemistry, The University of Birmingham, Birmingham,
B15 2TT, UK
Published online: 23 Sep 2006.
To cite this article: I. Basnak , P. L. Coe & R. T. Walker (1994) The Synthesis of Some 5-
Substituted-6-aza-2′-deoxyuridines, Nucleosides and Nucleotides, 13:1-3, 163-175, DOI:
10.1080/15257779408013233
To link to this article: http://dx.doi.org/10.1080/15257779408013233
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