82921-64-0Relevant academic research and scientific papers
Chemoselective and Diastereoselective Synthesis of C-Aryl Nucleoside Analogues by Nickel-Catalyzed Cross-Coupling of Furanosyl Acetates with Aryl Iodides
Li, Chao,Li, Luyang,Li, Yuxi,Shao, Feng,Tian, Xiaoying,Wang, Zheng
supporting information, (2021/11/30)
Canonical nucleosides are vulnerable to enzymatic and chemical degradation, yet their stable mimics—C-aryl nucleosides—have demonstrated potential utility in medicinal chemistry, chemical biology, and synthetic biology, although current synthetic methods remain limited in terms of scope and selectivity. Herein, we report a cross-electrophile coupling to prepare C-aryl nucleoside analogues from readily available furanosyl acetates and aryl iodides. This nickel-catalyzed modular approach is characterized by mild reaction conditions, broad substrate scope, excellent β-selectivity, and high functional-group compatibility. The exclusive chemoselectivity with respect to the aryl iodide enables efficient preparation of a variety of C-aryl halide furanosides suitable for various downstream transformations. The practicality of this transformation is demonstrated through the synthesis of a potent analogue of a naturally occurring NF-κB activator.
Peracetylated β-allyl C-glycosides of D-ribofuranose and 2-deoxy-D-ribofuranose in the chemical literature: Until now, mirages in the literature
Martinez, Heike Otero,Reinke, Helmut,Michalik, Dirk,Vogel, Christian
body text, p. 1834 - 1840 (2010/02/28)
The peracetylated β-allyl C-glycosides of D-ribofuranose (8) and 2-deoxy-D-ribofuranose (13) were stereoselectively prepared via the isopropylidene derivatives 3 and 4. These reactions represent what are, to the best of our knowledge, the first preparation of these apparently simple derivatives whose structures were carefully proved by NMR and X-ray investigations. Publications which allegedly described the synthesis of 8 and 13 were critically examined. Georg Thieme Verlag Stuttgart.
