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首页> 外文期刊>European journal of organic chemistry >Intramolecular glycosidation by click reaction mediated spacer generation followed by spacer cleavage
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Intramolecular glycosidation by click reaction mediated spacer generation followed by spacer cleavage

机译：通过点击反应介导的间隔区生成，然后进行间隔区切割的分子内糖苷化

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摘要

2-O-Propargyl-substituted glycosyl donors and O-(2-azidobenzyl)-substituted acceptors having a vicinal hydroxy group readily underwent the click reaction. Intramolecular glycosidation with N-iodosuccinimide/trifluoromethansulfonic acid as the activating system afforded β-(1-3)- and α-(1-2)-linked disaccharides as part of 14-membered macrocycles. Descriptors for these reactions are proposed that consider the donor and acceptor attachment sites and the stereochemistry of the functional groups. Investigation of the influence of 2-O-linked 1-aryl-1,2,3-triazol-4-ylmethyl groups, as contained in the spacer, on the anomeric selectivity exhibited no anchimeric assistance. In addition, it was shown that the spacer group can be readily cleaved under Birch reduction conditions. The 1,2,3-triazole-forming click reaction was employed to generate glycosyl donor-spacer-acceptor constructs. Upon glycosidation, 14-membered macrocycles were obtained with high anomeric selectivity. Spacer cleavage was performed under Birch reduction conditions.
机译：具有邻位羟基的2-O-炔丙基取代的糖基供体和O-（2-叠氮基苄基）取代的受体容易发生点击反应。用N-碘琥珀酰亚胺/三氟甲磺酸作为活化系统进行分子内糖苷化反应，得到β-（1-3）-和α-（1-2）-连接的二糖，作为14元大环的一部分。提出了考虑到供体和受体连接位点以及官能团的立体化学的这些反应的描述子。对包含在间隔基中的2-O-连接的1-芳基-1,2-1,2,3-三唑-4-基甲基的影响对异头选择性的影响没有显示出任何辅助性。另外，显示了在桦木还原条件下可以容易地裂解间隔基。形成1,2,3-三唑的点击反应用于生成糖基供体-间隔子-受体构建体。糖苷化后，获得具有高异头选择性的14元大环。间隔物切割在桦木还原条件下进行。

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