Bromonium ion-promoted glycosidic bond formation and simultaneous bromination of an activated aryl aglycon.
N-Bromosuccinimide (NBS) together with a catalytic amount of Me(3)SiOTf was found to be effective for the activation of thioglycosides. Concurrently with formation of the glycosidic bond, bromination took place on the activated aromatic ring of a 4-methoxyphenyl aglycon.
Qin
Zhi-Hui
ZH
Department of Bioorganic Chemistry, School of Pharmaceutical Sciences, Beijing Medical University, Beijing 100083, PR China.
Li
Hui
H
Cai
Meng-Shen
MS
Li
Zhong-Jun
ZJ
D001966:Bromine / Q000737:chemistry*; D001974:Bromosuccinimide / Q000737:chemistry*; D004187:Disaccharides / Q000138:chemical synthesis* / Q000737:chemistry; D013863:Thioglucosides / Q000737:chemistry*
D004187:Disaccharides; D013863:Thioglucosides; D001974:Bromosuccinimide; D001966:Bromine