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 (Tf2O) at −78 °C. The glycosyl acceptor was added to the reaction mixture at the same temperature to furnish various disaccharide, including the protected Lewis a (Lea) trisaccharide, in good yields.

Figure optionsDownload as PowerPoint slide