De novo asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide
De novo asymmetric synthesis of anthrax tetrasaccharide and related tetrasaccharide
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DOI：
10.1021/jo800691v
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发表时间：
2008-07-18
影响因子：
3.6
通讯作者：
O'Doherty, George A.
中科院分区：
文献类型：
--
作者：
Guo, Haibing;O'Doherty, George A.
以乙酰呋喃为原料，建立了天然产物炭疽四糖I及其异构化己基叠氮基类似物2的不对称从头合成方法。四糖的构建是通过传统的[3+1]糖基化策略实现的。通过迭代非对映选择性钯催化的糖基化、Luche还原、非对映选择性二羟基化和区域选择性酰化反应组装了L-鼠李糖三糖构建块。除了Luche还原和二羟基化外，人类的构筑基团还需要钯催化的叠氮烯丙基化和三氟代转化来设定葡萄糖立体化学。
A de novo asymmetric approach to the natural product anthrax tetrasaccharide I and an analogue 2 with an anomeric hexyl azide group has been developed from acetylfuran. The construction of the tetrasaccharide was achieved by a traditional [3 + 1] glycosylation strategy. An iterative diastereoselective palladium-catalyzed glycosylation, Luche reduction, diastereoselective dihydroxylation, and regioselective acylation were employed for the assembly of the L-rhamno-trisaccharide building block. The anthrose building block also required a palladium-catalyzed azide allylation and a triflate inversion to set the glucostereochemistry in addition to Luche reduction and dihydroxylation.