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首页> 外文会议>International Carbohydrate Symposium >THE ACYLOXYALLYLATION OF (UN)PROTECTED TETROSES REVEALING A PRONOUNCED DIASTEREODIVERGENCE AND A FUNDAMENTAL DIFFERENCE IN THE PERFORMANCE OF THE MEDIATING METAL
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THE ACYLOXYALLYLATION OF (UN)PROTECTED TETROSES REVEALING A PRONOUNCED DIASTEREODIVERGENCE AND A FUNDAMENTAL DIFFERENCE IN THE PERFORMANCE OF THE MEDIATING METAL

机译：（联合国）的酰氧基术术术术辐射透露介于介质金属性能的显着的差异和对​​介质性能的根本差异

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摘要

The acyloxyaflylation of unprotected aldoses was first demonstrated more than a decade ago as an elegant two-carbon homologation of reducing sugars (upon ozonolysis) [1], however, its application in real case syntheses remained scarce. Following up on such a successful show-case (short and scalable synthesis of the important bacterial sugar L-glycero-D-manno-heptose [2]) and to address several pending questions about this attractive transformation, we engaged in an in depth methodological re-investigation. The epimeric tetroses L-erythrose and D-threose in unprotected and protected aldehyde form were successfully applied to the indium and also zinc mediated acyloxyallylation, the latter being a first for an unprotected sugar. The investigation largely benefited from the choice of these more exotic starting materials as it allowed unambiguous identification of all hexose-products (authentic reference materials) as well as the reliable quantification of all diastereomers formed, even at very low proportions.
机译：首先在未经保护的醛固链烷烃的酰氧基氧化酰胺超过十年前作为还原糖（臭氧）的优雅两种碳成像[1]，然而，其在实际情况合成中的应用仍然稀缺。跟进这样一个成功的展示（重要的细菌糖L-甘油-D-manno-heptose [2]）并解决了关于这种有吸引力的转变的几个待解决问题，我们从事深度方法论重新调查。在未受保护和保护的醛形式中的缩醛四氧化术和D曲率成功地应用于铟，并且还介导的酰氧基溶解，后者是未受保护的糖的第一。该调查主要受益于这些更加异种的起始材料的选择，因为它允许明确的所有己糖产品（真实参考材料）以及即使在非常低的比例下也形成的所有非对映异构体的可靠量化。

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