通过酸介导的同时脱苄基-乙酰解反应简便且区域选择性地制备部分O-苄基化的D-吡喃葡萄糖醋酸酯。
Facile and regioselective preparation of partly O-benzylated D-glucopyranose acetates via acid-mediated simultaneous debenzylation-acetolysis.
作者信息
Cao Yang, Okada Yasunori, Yamada Hidetoshi
机构信息
School of Science and Technology, Kwansei Gakuin University, 2-1 Gakuen, Sanda 669-1337, Japan.
出版信息
Carbohydr Res. 2006 Sep 25;341(13):2219-23. doi: 10.1016/j.carres.2006.05.018. Epub 2006 Jun 27.
Fully O-benzylated methyl alpha-D-glucopyranoside shows a steady order in stepwise debenzylation when it is treated with sulfuric acid in acetic anhydride. Based on the order of debenzylation, regioselective preparations of 2,3,4-tri-, 2,3-, 2,4-, 3,4-di-, and 2-O-benzyl-D-glucopyranose acetates were facilitated in greater than 80% yields. The key points of the preparative reactions were the control of the acid strength and choice of suitable substrates.
全O-苄基化的α-D-吡喃葡萄糖苷在用乙酸酐中的硫酸处理时，在逐步脱苄基过程中显示出稳定的顺序。基于脱苄基的顺序，以大于80%的产率促进了2,3,4-三-O-苄基、2,3-二-O-苄基、2,4-二-O-苄基、3,4-二-O-苄基和2-O-苄基-D-吡喃葡萄糖乙酸酯的区域选择性制备。制备反应的关键要点是酸强度的控制和合适底物的选择。
Zotero 插件