114967-51-0Relevant articles and documents
Direct dehydrative glycosylation catalyzed by diphenylammonium triflate
Hsu, Mei-Yuan,Lam, Sarah,Lin, Mei-Huei,Lin, Su-Ching,Wang, Cheng-Chung,Wu, Chia-Hui
supporting information, (2020/03/13)
Methods for direct dehydrative glycosylations of carbohydrate hemiacetals catalyzed by diphenylammonium triflate under microwave irradiation are described. Both armed and disarmed glycosyl-C1-hemiacetal donors were efficiently glycosylated in moderate to excellent yields without the need for any drying agents and stoichiometric additives. This method has been successfully applied to a solid-phase glycosylation.
Remote Participation during Glycosylation Reactions of Galactose Building Blocks: Direct Evidence from Cryogenic Vibrational Spectroscopy
Marianski, Mateusz,Mucha, Eike,Greis, Kim,Moon, Sooyeon,Pardo, Alonso,Kirschbaum, Carla,Thomas, Daniel A.,Meijer, Gerard,von Helden, Gert,Gilmore, Kerry,Seeberger, Peter H.,Pagel, Kevin
supporting information, p. 6166 - 6171 (2020/03/10)
The stereoselective formation of 1,2-cis-glycosidic bonds is challenging. However, 1,2-cis-selectivity can be induced by remote participation of C4 or C6 ester groups. Reactions involving remote participation are believed to proceed via a key ionic intermediate, the glycosyl cation. Although mechanistic pathways were postulated many years ago, the structure of the reaction intermediates remained elusive owing to their short-lived nature. Herein, we unravel the structure of glycosyl cations involved in remote participation reactions via cryogenic vibrational spectroscopy and first principles theory. Acetyl groups at C4 ensure α-selective galactosylations by forming a covalent bond to the anomeric carbon in dioxolenium-type ions. Unexpectedly, also benzyl ether protecting groups can engage in remote participation and promote the stereoselective formation of 1,2-cis-glycosidic bonds.
Visible light promoted method for constructing O-glycoside bonds
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Paragraph 0028-0029, (2020/07/13)
The invention discloses a visible light promoted method for constructing O-glycoside bonds. Glycosyl trichloroacetimidate is taken as a donor, and phenolic compounds are taken as a photocatalyst; a molecular sieve is added; and the O-glycoside bonds are g