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鸟苷和2'-脱氧鸟苷在C6位的官能化：一种改进的阿佩尔反应及咪唑的亲核芳香取代反应

Functionalization of guanosine and 2'-deoxyguanosine at C6: a modified Appel process and S(N)Ar displacement of imidazole.

作者信息

Janeba Zlatko, Lin Xiaoyu, Robins Morris J

机构信息

Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.

出版信息

Nucleosides Nucleotides Nucleic Acids. 2004;23(1-2):137-47. doi: 10.1081/ncn-120027823.

DOI:10.1081/ncn-120027823
PMID:15043142
Abstract

Treatment of sugar-protected 2-N-trityl derivatives of guanosine and 2'-deoxyguanosine with imidazole/triphenylphosphine/iodine/ethyldiisopropylamine gives the corresponding 6-(imidazol-1-yl)-2-(tritylamino)purine nucleosides. S(N)Ar displacement of the imidazole moiety with nucleophiles provides 2-amino-6-substituted-purine nucleosides and 2'-deoxynucleosides.

摘要

用咪唑/三苯基膦/碘/二异丙基乙胺处理鸟苷和2'-脱氧鸟苷的糖保护2-N-三苯甲基衍生物，得到相应的6-(咪唑-1-基)-2-(三苯甲基氨基)嘌呤核苷。亲核试剂对咪唑部分的S(N)Ar取代反应可得到2-氨基-6-取代嘌呤核苷和2'-脱氧核苷。

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