General method for the synthesis of 2′-azido-2′,3′-dideoxynucleosides by the use of [1,2]-hydride shift and β-elimination reactions
General method for the synthesis of 2′-azido-2′,3′-dideoxynucleosides by the use of [1,2]-hydride shift and β-elimination reactions
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利用[1,2]-氢化物移位和β-消除反应合成2-叠氮基-2,3-二脱氧核苷的通用方法
DOI：
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发表时间：
1992
期刊：
影响因子：
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通讯作者：
H. Kuzuhara
中科院分区：
文献类型：
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作者：
M. Kawana;H. Kuzuhara
以嘧啶核苷和嘌呤核苷为原料，通过磺酰化核苷的脱氧[1，2]-氢化物移位和β-消除反应得到3′-脱氧-“阿糖基”核苷，经6步反应合成了标题核苷（16 U，C，G和H），总收率约30%。从相应的鸟嘌呤核苷制备黄嘌呤类似物（9 X和16 X）。未保护的3′-脱氧-“阿拉伯糖”-核苷（9 U、C、A、G、H、X）及其叠氮核苷16在体外对HIV或小鼠P388白血病均未显示出任何显著活性。
The title nucleosides (16U, C, G and H) were synthesized from pyrimidine and purine ribonucleosides in about 30% overall yield in 6 steps via key intermediates, protected 3′-deoxy-‘arabino’-nucleosides, which were obtained by deoxygenative [1,2]-hydride shift and β-elimination reactions of sulfonylated ribo-counterparts. Xanthine analogues (9X and 16X) were prepared from the corresponding guanine nucleosides. The unprotected 3′-deoxy-‘arabino’-nucleosides (9U,C,A,G,H,X) and their azido nucleosides 16 did not show any significant activity against either HIV in vitro or P388 leukaemia in mice.
2-叠氮基-2,3-二脱氧嘧啶核苷。
影响因子：
7.3
作者：
Warshaw,JA;Watanabe,KA
通讯作者：
Watanabe,KA