化学
炔丙基
环加成
部分
叠氮化物
苷元
炔丙醇
胺气处理
戒指(化学)
立体化学
反应性(心理学)
糖基化
炔烃
组合化学
点击化学
有机化学
糖苷
催化作用
替代医学
病理
医学
生物化学
作者
Cristin Bosko,Raghu Vannam,Mark W. Peczuh
标识
DOI:10.1016/j.tetlet.2022.153699
摘要
• The report details a new synthetic route to 3-amino septanosides starting from furanosyl amines. • Structures of 3R and 3S configured α- and β-septanosides were characterized by NMR spectroscopy. • Septanoside formation by glycosidation enables the attachment of reactivity handles onto the aglycone. • Propargyl 3-amino septanosides were derivatized by click cycloaddition reactions. Amino pyranosides are an important component of natural products like vancomycin and erythromycin. The amine moiety mediates interactions with the biological targets of the compounds and it also influences physicochemical properties. Seven-membered ring septanose carbohydrates hold potential as ring-expanded glycomimetics of pyranosides. Methods for the synthesis of septanose carbohydrates are an essential pre-requisite for their broader application in chemical glycobiology and medicinal chemistry. Here we present the first reported synthesis of 3-aminoseptanosides. Starting from d -ribofuranose, the synthesis Key steps in the sequence include addition by allyl Grignard to a furanosyl amine, ozonolysis, and glycosidation to form the seven-membered ring. Importantly, glycosidation with alcohols like propargyl alcohol introduced a reactivity handle onto the aglycon. Propargyl 3-amino septanosides were subjected to alkyne-azide click cycloaddition reactions with representative azides. This exercise illustrated the post-glycosylation diversification of septanosides, linking our interest in ring-expanded glycomimetics and methods for preparing collections of glycosylated small molecules.
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