The synthesis of 1′-azido C-nucleosides is described to expand the set of azide-functionalized nucleosides for bioorthogonal applications and as potential antiviral drugs. Lewis acid-promoted azidation of a nucleoside hemiketal resulted in the formation of a tetrazole through a Schmidt reaction manifold. Conformational control to prevent ring–chain tautomerism enabled efficient 1′-azidation with complete β-diastereoselectivity. The unique reactivity and further derivation of the 1′-azido C-nucleosides are also reported.

中文翻译：

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保护羟基酮-半基互变异构平衡的基团控制能够立体选择性合成 1′-叠氮基 C-核苷


1′-叠氮基 C-核苷的合成被描述为扩展叠氮化物官能化核苷的集合，用于生物正交应用和作为潜在的抗病毒药物。路易斯酸促进的核苷半脑胶氮化导致通过 Schmidt 反应歧管形成四唑。防止环链互变异构体的构象控制实现了高效的 1′-叠氮化和完全的 β-非对映选择性。还报道了 1′-叠氮基 C-核苷的独特反应性和进一步衍生。