77870-93-0Relevant 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.
Un nouvel agent de glycosylation: l'anhydride trifluoromethanesulfonique. Synthese des α et β O-glycosyl-L-serine, -L-threonine et -L-hydroxyproline
Lacombe, J. M.,Pavia A. A.,Rocheville, J. M.
, p. 473 - 481 (2007/10/02)
When 2,3,4,6-tetra-O-benzyl-D-glucopyranose, -D-galactopyranose and 2,3,4-tri-O-benzyl-D-xylopyranose were allowed to react in the cold in dichloromethane or acetonitrile as solvent in the presence of trifluoromethanesulfonic (triflic) anhydride, with methyl or benzyl esters of the N-(benzyloxycarbonyl)-L-serine, -L-threonine, and -L-hydroxyproline, an anomeric mixture of the corresponding O-glycosylaminoacids was obtained (55 to 90percent overall yield), with the α-anomer being predominant.The same experimental procedure was successfully applied to the condensation of the benzyl ester of the N-(benzyloxycarbonyl)-L-hydroxyproline with 2,3,4-tri-O-benzyl-L-arabinopyranose and 2,3,5-tri-O-benzyl-L-arabinofuranose affording the corresponding condensation products with similar yield.Pure α and β anomers were obtained after column chromatography or crystallization with 30 to 65percent yield.Hydrogenolysis of benzyl derivatives afforded the unprotected compounds.Optical rotation, (1)H and (13)C nmr were the main methods used to assess structure and stereochemistry.
