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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.

DOI:10.1021/acs.joc.4c01484
PMID:39137335
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11384238/
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。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/f2d8b2c3baad/nihms-2016719-f0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/862fa8ba4496/nihms-2016719-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/f37078d24dfb/nihms-2016719-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/177075318072/nihms-2016719-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/eab039237ade/nihms-2016719-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/b3c27a50bcf7/nihms-2016719-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/54f9cb22d408/nihms-2016719-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/f2d8b2c3baad/nihms-2016719-f0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/862fa8ba4496/nihms-2016719-f0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/f37078d24dfb/nihms-2016719-f0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/177075318072/nihms-2016719-f0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/eab039237ade/nihms-2016719-f0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/b3c27a50bcf7/nihms-2016719-f0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/54f9cb22d408/nihms-2016719-f0007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e3f7/11384238/f2d8b2c3baad/nihms-2016719-f0008.jpg

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