[2-(15)N]鸟苷和2'-脱氧[2-(15)N]鸟苷衍生物的高效合成。

Efficient syntheses of [2-(15)N]guanosine and 2'-deoxy[2-(15)N]guanosine derivatives.

作者信息

Kamaike Kazuo, Kayama Yoshihiro, Isobe Mitsuhisa, Kawashima Etsuko

机构信息

Laboratory of Pharmaceutical Chemistry, School of Pharmacy, Tokyo University of Pharmacy and Life Science, 1432-1 Horinouchi, Hachioji, Tokyo 192-0392, Japan.

出版信息

Nucleic Acids Symp Ser (Oxf). 2004(48):53-4. doi: 10.1093/nass/48.1.53.

DOI:10.1093/nass/48.1.53

PMID:17150474

Abstract

Nucleophilic substitution of 9-(2,3,5-tri-O-acetyl-beta-D-ribofuranosyl)-6-chloro-2-fluoro-9H-purine, prepared from guanosine, with N-tert-butyldimethylsilyl[(15)N]-phthalimide in the presence of a catalytic amount of CsF at room temperature in DMF efficiently afforded the 6-chloro-2-[(15)N]phthalimidopurine derivative. Treatment of this with sodium 2-cyanoethoxide yielded the [2-(15)N]guanosine derivative. The 2'-deoxy[2-(15)N]guanosine derivative was also efficiently synthesized through a similar procedure.

摘要

由鸟苷制备的9-(2,3,5-三-O-乙酰基-β-D-呋喃核糖基)-6-氯-2-氟-9H-嘌呤在室温下于N,N-二甲基甲酰胺中，在催化量的氟化铯存在下与N-叔丁基二甲基甲硅烷基[(15)N]-邻苯二甲酰亚胺进行亲核取代反应，高效地得到了6-氯-2-[(15)N]邻苯二甲酰亚胺基嘌呤衍生物。用2-氰基乙醇钠处理该产物得到[2-(15)N]鸟苷衍生物。2'-脱氧[2-(15)N]鸟苷衍生物也通过类似的步骤高效合成。