Title:Recent Advances in the Synthesis of 5′-deoxynucleoside Phosphonate
Analogs
Volume: 29
Issue: 22
关键词:
5′-脱氧核苷磷酸盐,抗病毒药物,酶抑制剂,生物电子等排体,核苷,核苷类似物
摘要: The present review focuses on the synthesis of cyclic 5′-deoxynucleoside
phosphonate analogs. The formation of various phosphonate alkyl moieties is accomplished
through (i) Wittig (or HWE) type condensation to the nucleoside aldehyde moiety;
(ii) nucleophilic displacement reaction using phosphonate anion or Lewis acid; (iii)
Arbuzov reaction; (iv) olefin cross-metathesis between vinyl phosphonates and vinylated
nucleosides; and (v) radical reaction and Pd catalyzed alkyne. For the coupling of nucleobases
with cyclic moieties, the Mitsunobu reaction and Sonogashira-type cross-coupling
are usually applied. For the coupling of furanose moieties with nucleobases, Vorbrüggentype
condensation is generally applied. Addition reactions mediated by selenium ions are
mainly applied for the coupling of carbocyclic moieties. Their biological activity results
have been summarized.