氢键介导的苷元传递反应在β-葡萄糖苷合成中的应用研究。
Investigation of the H-bond-mediated aglycone delivery reaction in application to the synthesis of β-glucosides.
作者信息
Mannino Michael P, Yasomanee Jagodige P, Demchenko Alexei V
机构信息
Department of Chemistry and Biochemistry, University of Missouri - St. Louis One University Boulevard, St. Louis, MO, 63121, USA.
Department of Chemistry and Biochemistry, University of Missouri - St. Louis One University Boulevard, St. Louis, MO, 63121, USA.
出版信息
Carbohydr Res. 2018 Dec;470:1-7. doi: 10.1016/j.carres.2018.09.003. Epub 2018 Sep 22.
Abstract
In an attempt to refine the H-bond-mediated Aglycone Delivery (HAD) glycosylation reaction reported herein is the synthesis of β-glucosides using an ethylthio glucoside donor equipped with the remote 6-O-picoloyl substituent. Upon examining various aliphatic, aromatic, and carbohydrate acceptors, it was determined that both electronic and steric factors may greatly affect the stereoselectivity of the HAD reaction with this donor.
摘要
为了优化本文报道的氢键介导的苷元递送（HAD）糖基化反应，使用配备有远程6-O-吡啶甲酰基取代基的乙硫基葡萄糖苷供体合成了β-葡萄糖苷。在研究各种脂肪族、芳香族和碳水化合物受体时，发现电子和空间因素都可能极大地影响该供体参与的HAD反应的立体选择性。
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