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Development of Glycosylation Protocols Using Glycosyl N-Phenylethynyl Pyrrole-2-carboxylates as Donors
Organic Letters ( IF 4.9 ) Pub Date : 2024-11-12 , DOI: 10.1021/acs.orglett.4c03768
Mengyu Li, Li Song, Liya Yang, Yitian Zhao, Meifang Yang, Houchao Tao

We herein introduce glycosyl N-phenylethynyl pyrrole-2-carboxylates (PEPCs) as novel and highly efficient glycosyl donors. The unique inclusion of the pyrrole group, serving as both an electron-donating group and an ortho-tethering scaffold, imparts exceptional shelf stability while retaining reactivity for glycosylation reactions. PEPC donors exhibit broad utility for both O- and N-glycosylation across a variety of substrates. Additionally, their versatility and efficiency were further demonstrated in a one-pot saccharide synthesis, showcasing their potential for diverse synthetic applications.

中文翻译:


使用糖基 N-苯乙炔基吡咯-2-羧酸盐作为供体的糖基化方案的开发



我们在此介绍糖基 N-苯乙基吡咯-2-羧酸盐 (PEPCs) 作为新型且高效的糖基供体。吡咯基团的独特内含物,既是电子供体基团,又是邻位栓系支架,赋予了卓越的货架稳定性,同时保持了糖基化反应的反应性。PEPC 供体在各种底物的 O-和 N-糖基化方面表现出广泛的实用性。此外,它们的多功能性和效率在一锅法糖类合成中得到了进一步证明,展示了它们在多种合成应用方面的潜力。
更新日期:2024-11-12
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