1038412-58-6Relevant articles and documents
A straightforward and versatile FeCl3 catalyzed Friedel-Crafts C-glycosylation process. Application to the synthesis of new functionalized C-nucleosides
Tachallait, Hamza,Safir Filho, Mauro,Marzag, Hamid,Bougrin, Khalid,Demange, Luc,Martin, Anthony R.,Benhida, Rachid
supporting information, p. 5551 - 5558 (2019/04/04)
A new, straightforward and eco-compatible route to C-(hetero)aryl nucleosides is reported. This ribosylation process consists of a one-step FeCl3 catalyzed Friedel-Crafts β-C-glycosydation reaction. This reaction occurs through an oxonium intermediate from readily available protected sugars leading to functionalized C-nucleosides with high stereocontrol. The expected new C-nucleosides were obtained in good yields within a short reaction time (10 min). Moreover, this approach is compatible with the use of a range of bulky (poly)aromatics such as naphthalene, anthracene and pyrene, which are not easily accessible via classical routes. These new C-aryl-nucleosides exhibit interesting photophysical properties, underling their potential use for further nucleic acid labelling.
Friedel-Crafts and modified Vorbrüggen ribosylation. A short synthesis of aryl and heteroaryl-C-nucleosides
Spadafora, Marie,Mehiri, Mohamed,Burger, Alain,Benhida, Rachid
, p. 3967 - 3971 (2008/09/20)
A direct coupling of aryl donor and tetra-O-acetylribose in the presence of Lewis acid led to β-C-nucleosides in good yields. In contrast, for deactivated electron-poor aromatics, a modified Vorbru?ggen ribosylation reaction was investigated and successfully applied in the case of 2-trimethylsilyl-thiazole.
