Yu, Fei; Dickson, Jalen L.; Loka, Ravi S.; Xu, Hengfu; Schaugaard, Richard N.; Schlegel, H. Bernhard; Luo, Long; Nguyen, Hien M. published the artcile< Diastereoselective sp3 C-O Bond Formation via Visible Light-Induced, Copper-Catalyzed Cross-Couplings of Glycosyl Bromides with Aliphatic Alcohols>, Application of C12H20O6, the main research area is LED copper catalyzed diastereoselective coupling bromoglycoside aliphatic alc; C(sp3)–O bond; copper catalysis; cross-coupling; stereoselective; visible light.
Copper-catalyzed cross-coupling reactions have become one of the most powerful methods for generating carbon-heteroatom bonds, an important framework of many organic mols. However, copper-catalyzed C(sp3)-O cross-coupling of alkyl halides with alkyl alcs. remains elusive because of the sluggish nature of oxidative addition to copper. To address this challenge, we have developed a catalytic copper system, which overcomes the copper oxidative addition barrier with the aid of visible light and effectively facilitates the cross-couplings of glycosyl bromides with aliphatic alcs. to afford C(sp3)-O bonds with high levels of diastereoselectivity. Importantly, this catalytic system leads to a mild and efficient method for stereoselective construction of α-1,2-cis glycosides, which are of paramount importance, but challenging. In general, stereochem. outcomes in α-1,2-cis glycosidic C-O bond-forming processes are unpredictable and dependent on the steric and electronic nature of protecting groups bound to carbohydrate coupling partners. Currently, the most reliable approaches rely on the use of a chiral auxiliary or hydrogen-bond directing group at the C2- and C4-position of carbohydrate electrophiles to control α-1,2-cis selectivity. In our approach, earth-abundant copper not only acts as a photocatalyst and a bond-forming catalyst, but also enforces the stereocontrolled formation of anomeric C-O bonds. This cross-coupling protocol enables highly diastereoselective access to a wide variety of α-1,2-cis-glycosides and biol. relevant α-glycan oligosaccharides. Our work provides a foundation for developing new methods for the stereoselective construction of natural and unnatural anomeric carbon(sp3)-heteroatom bonds.
ACS Catalysis published new progress about Alcohols Role: RCT (Reactant), RACT (Reactant or Reagent) (glycoside). 4064-06-6 belongs to class alcohols-buliding-blocks, and the molecular formula is C12H20O6, Application of C12H20O6.
Referemce:
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts