62983-62-4Relevant articles and documents
Copper-Catalyzed Anomeric O-Arylation of Carbohydrate Derivatives at Room Temperature
Verdelet, Tristan,Benmahdjoub, Sara,Benmerad, Belkacem,Alami, Mouad,Messaoudi, Samir
, p. 9226 - 9238 (2019/08/12)
Direct and practical anomeric O-arylation of sugar lactols with substituted arylboronic acids has been established. Using copper catalysis at room temperature under an air atmosphere, the protocol proved to be general, and a variety of aryl O-glycosides have been prepared in good to excellent yields. Furthermore, this approach was extended successfully to unprotected carbohydrates, including α-mannose, and it was demonstrated here how the interaction between carbohydrates and boronic acids can be combined with copper catalysis to achieve selective anomeric O-arylation.
Novel Synthesis of Aryl 2,3,4,6-Tetra-O-acetyl-D-glucopyranosides
Yamaguchi, Masahiko,Horiguchi, Akira,Fukuda, Akira,Minami, Toru
, p. 1079 - 1082 (2007/10/02)
The glucosidation of phenols with 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl fluoride in the presence of BF3*OEt2 to give, predominantly, α-anomers has been studied.In the presence of an amine base, 1,1,3,3-tetramethylguanidine, however, enhanced β-selectivity was achieved.The former reaction provides a novel and useful synthesis of aryl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside whilst the latter is effective for the glycosidation of relatively hindered phenols.
