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首页> 外文期刊>Chemistry of heterocyclic compounds >Diastereoselective synthesis of some carbocyclic 2′-oxa-3′-aza-nucleosides
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Diastereoselective synthesis of some carbocyclic 2′-oxa-3′-aza-nucleosides

机译:一些碳环2'-oxa-3'-氮杂-核苷的非对映选择性合成

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摘要

Two strategies for the synthesis of isoxazolidinyl nucleosides as potential antiviral agents are reported: a one-step approach based on 1,3-dipolar cycloaddition of D-lyxosyl nitrone with N,N-dibenzyl-9-vinyl adenine, and a two-step methodology based on the Vorbrüggen nucleosidation of the 5-acetoxyisoxazolidine. The chiral D-lyxosyl nitrone undergoes regioselective 1,3-dipolar cycloadditions with N,N-dibenzyl-9-vinyl adenine and vinyl acetate giving 5-substituted isoxazolidines as a mixture of four diastereoisomers in good yields. The condensation of 5-acetoxyisoxazolidine with silylated uracil, thymine, and N-acetylcytosine proceeded with moderate to good stereoselectivity with the formation of the expected isoxazolidinyl β-and α-nucleosides.
机译:据报道,有两种合成异恶唑啉基核苷作为潜在抗病毒剂的策略:一种基于D-糖基硝酮与N,N-二苄基-9-乙烯基腺嘌呤的1,3-偶极环加成的一步法,以及一种两步法的方法基于5-乙酰氧基异唑烷的Vorbrüggen核苷化。手性D-二糖基硝酮与N,N-二苄基-9-乙烯基腺嘌呤和乙酸乙烯酯进行区域选择性的1,3-偶极环加成反应,以高收率得到5-取代的异恶唑烷,为四种非对映异构体的混合物。 5-乙酰氧基异恶唑烷与甲硅烷基化的尿嘧啶,胸腺嘧啶和N-乙酰胞嘧啶的缩合以中等至良好的立体选择性进行,形成了预期的异恶唑烷酰基β-和α-核苷。

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