Native sugars represent one of the most abundant classes of natural products, exhibiting a multitude of biological functions. Unsurprisingly, functionalized carbohydrates and their conjugates based on both mono-and oligosaccharides have found numerous applications in biochemistry, molecular biology, and medicine, in particular, for the development of new pharmaceutical and diagnostic agents. The synthetic efforts towards modified native sugars have traditionally focused on the regioselective functionalization of carbohydrate hydroxy groups and the stereoselective synthesis of functionalized Oglycosides. Subsequently, the lability of O-glycosidic bond under enzymatic conditions has stimulated the development of synthetic methods towards C-glycosides, which typically exhibit enhanced metabolic stability. Considerable efforts were also put fourth towards the synthesis of non-typical C-functionalized sugars (Fig. ), in which various structural motifs are appended to the nonanomeric C-centers. Importantly, such non-typical sugars are frequently found as metabolites in bacteria but not in mammals, making them an attractive synthetic target for the development of pharmaceutical agents with intrinsically low toxicity. Modification of the native sugar skeleton to access non-typical C-functionalized sugars has traditionally been achieved through tedious synthetic sequences featuring extensive use of protecting groups and unstable synthetic intermediates, such as keto-sugars (Fig. ). As an alternative, various metaland free radical-mediated sequences proceeding through C-H bond activation have been devised, but these methods has not gained widespread applicability due to being highly substrate-specific. A far more direct approach to non-typical C-functionalized sugars was contrived through intermolecular radicalmediated C-H bond activation propelled by photoredox catalysis (Fig. ). In these systems, Cfunctionalization of the carbohydrate skeleton of native sugars does not require the use of protecting groups and even employs the free hydroxy groups to promote the key C-H bond activation step with an aid of phosphorous, boron or tin-based co-catalysts. However, the intermolecular nature of the key hydrogen atom transfer (HAT) step in these manifolds severely limits the control over site-selectivity of the C-functionalization reaction. This challenge was most recently addressed in photoredox-mediated systems proceeding through intramolecular HAT, displaying predictable site-selectivity. However, the employed photoredox-active tethering groups both necessitated the protection of sugar hydroxy groups and required considerably harsh conditions for the removal of the tethering group after the Cfunctionalization reaction, decreasing the atom-economy and limiting the applicability of these systems. In this work, we sought to develop a photocatalytic system that allows for site-selective Cfunctionalization of native sugars with a traceless redox-active tethering group, providing a straightforward and general route to completely unprotected non-typical sugars (Fig. ).