Pre-activation of fully acetylated dodecyl thioglycosides with BSP-Tf2O led to efficient glycosylation at low temperature.
Fully acetylated dodecyl thioglycosides were found to be useful as glycosyl donors by activation with 1-benzenesulfinyl piperidine (BSP) and triflic anhydride (Tf(2)O) at -78 degrees C. The glycosyl acceptor was added to the reaction mixture at the same temperature to furnish various disaccharide, including the protected Lewis a (Le(a)) trisaccharide, in good yields.
Son
Sang-Hyun
SH
Graduate School of Environmental Science, Hokkaido University, Kita-ku, Sapporo 060-0810, Japan.
Tano
Chiharu
C
Furuike
Tetsuya
T
Sakairi
Nobuo
N
D000107:Acetylation; D002240:Carbohydrate Sequence; D003080:Cold Temperature; D005663:Furans / Q000737:chemistry*; D006031:Glycosylation; D008969:Molecular Sequence Data; D010880:Piperidines / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry*
C469850:1-(benzenesulfinyl)piperidine; D005663:Furans; D010880:Piperidines; D013449:Sulfonamides; D013865:Thioglycosides; C474725:triflic anhydride