Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations.
Stereoselective synthesis of protected l- and d-dideoxysugars and analogues via Prins cyclisations.
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DOI：
10.1039/c5sc04144a
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发表时间：
2016-04-21
期刊：
影响因子：
8.4
通讯作者：
Willis CL
中科院分区：
文献类型：
--
作者：
Beattie RJ;Hornsby TW;Craig G;Galan MC;Willis CL
硅缩醛与高烯丙醇环化生成甲硅烷基四氢吡喃，随后氧化，快速获得脱氧糖苷类似物。描述了一种用于快速构建正交保护的l-和d-脱氧糖及其类似物的从头方法。一种新颖的和稳健的硅缩醛经历Prins环化与一系列高烯丙醇在高产率和良好的立体控制。改进的Tamao-Fleming氧化法可以直接得到脱氧糖苷类似物，该方法在合成抗癌药物阿克拉霉素A的一种组分--保护的l-寡糖中得到了展示。
Cyclisation of a silicon acetal with homoallylic alcohols to generate silyltetrahydropyrans and subsequent oxidation gives rapid access to deoxyglycoside analogues. A de novo approach for the rapid construction of orthogonally protected l- and d-deoxysugars and analogues is described. A novel and robust silicon-acetal undergoes Prins cyclisations with a series of homoallylic alcohols in high yield and excellent stereocontrol. Modified Tamao–Fleming oxidation of the resulting silyltetrahydropyrans gives direct access to deoxyglycoside analogues and the approach was showcased in the synthesis of protected l-oliose, a component of the anticancer agent aclacinomycin A.