通过1-羟基苯并三唑介导的糖基半缩醛酰化反应立体选择性合成β-糖基酯
Stereoselective Synthesis of β-glycosyl Esters via 1-Hydroxybenzotriazole Mediated Acylation of Glycosyl Hemiacetals.
作者信息
Liu Zijing, Liu Dan, Zhu Dapeng, Yu Biao
机构信息
Key Laboratory of Structure-Based Drugs Design and Discovery of Ministry of Education, Shenyang Pharmaceutical University, Shenyang 110016, China.
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai 200032, China.
出版信息
Org Lett. 2023 Jul 21;25(28):5372-5377. doi: 10.1021/acs.orglett.3c01750. Epub 2023 Jul 12.
Highly stereoselective access to β-glycosyl esters was disclosed, employing 1-hydroxybenzotriazole (HOBt) mediated esterification of glycosyl hemiacetals in the presence of EDCI and 1,4-diazabicyclo[2.2.2]octane (DABCO). Mechanistic studies indicated a dynamic kinetic acylation pathway. In addition, a stereoretentive esterification of glycosyl hemiacetals with -butyloxycarbonyl -hexynylbenzoate and DMAP was also reported.
公开了一种高度立体选择性地合成β-糖基酯的方法，该方法采用1-羟基苯并三唑（HOBt）在1-乙基-3-(3-二甲基氨基丙基)碳二亚胺（EDCI）和1,4-二氮杂双环[2.2.2]辛烷（DABCO）存在下介导糖基半缩醛的酯化反应。机理研究表明这是一条动态动力学酰化途径。此外，还报道了糖基半缩醛与叔丁氧羰基-己炔基苯甲酸酯和4-二甲氨基吡啶（DMAP）的立体保持酯化反应。
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