1-C-受体取代的糖醛在酸促进（费歇尔重排）条件下与亲核试剂的反应。
Reactions of 1-C-acceptor-substituted glycals with nucleophiles under acid promoted (Ferrier-rearrangement) conditions.
机构信息
Department of Organic Chemistry, University of Debrecen, POB 400, H-4002, Debrecen, Hungary; University of Debrecen, Doctoral School of Chemistry, PO Box 400, H-4002, Debrecen, Hungary.
Department of Organic Chemistry, University of Debrecen, POB 400, H-4002, Debrecen, Hungary.
出版信息
Carbohydr Res. 2022 Sep;519:108582. doi: 10.1016/j.carres.2022.108582. Epub 2022 May 10.
The reactivity of O-peracetylated and O-perbenzoylated 1-COOMe, 1-CONH and 1-CN-substituted glycals was studied against O-, S-, N- and C-nucleophiles in the presence of Lewis acids. Allylic substituted products with exclusive axial stereoselectivity were formed with simple alcohols, N, and Cl ions, but with benzyl thiol the Ferrier rearrangement took place and thioglycosides were obtained. The use of a sugar derived thiol resulted in the formation of both the allylic substituted and the rearranged products.
研究了 O-乙酰化和 O-苯甲酰化的 1-COOMe、1-CONH 和 1-CN 取代的糖醛在路易斯酸存在下与 O、S、N 和 C 亲核试剂的反应性。与简单醇、N 和 Cl 离子反应时，生成具有立体选择性的轴向产物，但与苄硫醇反应时发生 Ferrier 重排，得到硫代糖苷。使用衍生自糖的硫醇会形成取代产物和重排产物。
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