通过固-液相转移糖基化法合成5-氮杂-7-脱氮嘌呤和3,7-二脱氮嘌呤2'-脱氧呋喃核糖苷
Synthesis of 5-aza-7-deazapurine and 3,7-dideazapurine 2'-deoxyribofuranosides by solid-liquid phase-transfer glycosylation.
作者信息
Seela F, Rosemeyer H, Bourgeois W
机构信息
Laboratorium für Organische und Bioorganische Chemie, Universität Osnabrück, FRG.
出版信息
Nucleic Acids Symp Ser. 1987(18):49-52.
PMID:3697149
Abstract
The 2'-deoxyguanosine isostere 1 as well as the pyrrolo [3,2-c] pyridine 2'-deoxyribofuranosides 2a,b and 3a-d have been synthesized in high yield by solid-liquid phase-transfer glycosylation. It was shown that only the strongly nucleophilic pyrrolo [3,2-c] pyridines formed exclusively beta-2'-deoxyribofuranosides, whereas weakly nucleophilic imidazo [1,2-a]-s-triazines gave mixtures of anomers.
摘要
通过固-液相转移糖基化反应已高产率合成了2'-脱氧鸟苷类似物1以及吡咯并[3,2-c]吡啶2'-脱氧呋喃核糖苷2a、b和3a - d。结果表明，只有强亲核性的吡咯并[3,2-c]吡啶专一性地形成β-2'-脱氧呋喃核糖苷，而弱亲核性的咪唑并[1,2-a]-均三嗪则生成端基异构体的混合物。
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