采用阳离子金（I）催化的涉及糖基-1,1-二甲基炔丙基碳酸酯供体的糖苷化反应合成抗原性四糖重复单元。
Synthesis of Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl -1,1-Dimethylpropargyl Carbamate Donors.
机构信息
Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, Ohio 43606, United States.
出版信息
J Org Chem. 2024 Sep 6;89(17):12547-12558. doi: 10.1021/acs.joc.4c01484. Epub 2024 Aug 13.
Abstract
Synthesis of an antigenic tetrasaccharide repeating unit of the -polysaccharide of lipopolysaccharide has been accomplished. Those four monosaccharides were assembled stereoselectively by employing our recently developed cationic gold(I)-catalyzed glycosylation methodology involving various glycosyl -1,1-dimethylpropargyl carbamate donors. The newly formed α-anomeric stereochemical configuration was controlled by the axial C2-OBz of the glycosyl donors via anchimeric assistance.
摘要
已成功合成脂多糖的 -多糖的一个四糖重复单元抗原。这四种单糖通过采用我们最近开发的阳离子金（I）催化的糖基化方法立体选择性地组装，其中涉及各种糖基 -1,1-二甲基炔丙基碳酸酯供体。新形成的 α-端构型的立体化学构型通过糖基供体的轴向 C2-OBz 经由分子内协助进行控制。
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