Versatile synthesis and mechanism of activation of S-benzoxazolyl glycosides.
As a part of a program for developing new efficient procedures for stereoselective glycosylation, a range of S-benzoxazolyl (SBox) glycosides have been synthesized. The mechanistic aspects of the SBox moiety activation for glycosylation via a variety of conceptually different pathways in the presence of thiophilic, electrophilic, or metal-based promoters have been investigated.
Kamat
Medha N
MN
Department of Chemistry and Biochemistry, University of Missouri-St. Louis, One University Boulevard, St. Louis, Missouri 63121, USA.
Rath
Nigam P
NP
Demchenko
Alexei V
AV
D000478:Alkylation; D001583:Benzoxazoles / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D006027:Glycosides / Q000138:chemical synthesis / Q000737:chemistry*; D007477:Ions / Q000737:chemistry; D008670:Metals / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011522:Protons
D001583:Benzoxazoles; D006027:Glycosides; D007477:Ions; D008670:Metals; D011522:Protons