|
|||||
|
|
Regio- and stereoselective glycosylation of 2-(o-dihydroxyborylbenzyl) thioglucoside and unprotected methyl glycosides |
|
| Authors: | Sarah Lam Mei-Yuan Hsu Cheng-Chung Wang |
| Institution: | 1. Institute of Chemistry, Academia Sinica, Taipei, Taiwan;2. Institute of Chemistry, Academia Sinica, Taipei, Taiwan
Chemical Biology and Molecular Biophysics Program, Taiwan International Graduate Program (TIGP), Academia Sinica, Taipei, Taiwan |
| Abstract: | A highly regio- and stereoselective glycosylation of a boronic acid-containing thioglucoside and unprotected methyl glycosides is described. A boronic acid moiety was installed at the ortho-position of the 2-O-benzyl group of a thioglucosyl donor. This provides transient partial protection for the unprotected glycosyl acceptor upon condensation and concomitantly prearranged the acceptor with respect to the donor for the ensuing intramolecular glycosylation. |
| Keywords: | boronic acid glycosylation regioselectivity stereoselectivity |