由d-苏氨酸合成l-柠檬糖硫苷供体。
ynthesis of an l-Lemonose Thioglycoside Donor from d-Threonine.
作者信息
Huseman Eric D, Townsend Steven D
机构信息
Department of Chemistry, Vanderbilt University, Nashville, TN 37235, USA.
出版信息
Tetrahedron Lett. 2021 Jun 8;73. doi: 10.1016/j.tetlet.2021.153097. Epub 2021 Apr 22.
Abstract
A short synthesis of an l-lemonose thioglycoside is described starting from d-threonine. The synthesis leverages a Dieckmann condensation and Stork-Danheiser transposition to arrive at a key vinylogous ester intermediate on gram scale. Ensuing 1,2-addition diastereoselectively establishes the C3 tetra-substituted center and subsequent glycal hydration allows for anomeric functionalization to the thioglycoside. H and NOESY NMR analyses reveal that the major α-anomer of thioglycoside deviates from the expected C conformation.
摘要
描述了一种从d-苏氨酸开始的L-甘露糖硫苷的简短合成方法。该合成利用迪克曼缩合反应和斯托克-丹海泽重排反应，以克级规模得到关键的乙烯酮酯中间体。随后的1,2-加成反应非对映选择性地构建了C3四取代中心，接着进行糖烯水合反应，实现硫苷的异头官能化。氢谱和NOESY核磁共振分析表明，硫苷的主要α-异头物偏离了预期的C构象。
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