S-Benzoxazolyl (SBox) glycosides as novel, versatile glycosyl donors for stereoselective 1,2-cis glycosylation.
[reaction: see text] Novel glycosyl donors, S-benzoxazolyl (SBox) glycosides, have been synthesized, tested toward various protecting group manipulations, and applied to the highly stereoselective 1,2-cis glycosylation. These compounds fulfill the requirements for a modern glycosyl donor such as accessibility, high stability toward protecting group manipulations, and mild activation conditions. It was also demonstrated that SBox glycosides withstand other glycosyl donor activation conditions and therefore allow selective glycosylations of O-pentenyl and thioglycosides.
Demchenko
Alexei V
AV
Department of Chemistry and Biochemistry, University of Missouri-St. Louis, 8001 Natural Bridge Road, St. Louis, Missouri 63121, USA. demchenkoa@umsl.edu
Malysheva
Nelli N
NN
De Meo
Cristina
C
D000171:Acrolein / Q000737:chemistry; D000179:Acrylates / Q000737:chemistry; D006031:Glycosylation; D007783:Lactones / Q000138:chemical synthesis; D010984:Platinum; D012428:Ruthenium; D013237:Stereoisomerism; D013865:Thioglycosides / Q000737:chemistry*
D000179:Acrylates; D007783:Lactones; D013865:Thioglycosides; D010984:Platinum; D000171:Acrolein; D012428:Ruthenium; C036658:acrylic acid