Superarming the S-benzoxazolyl glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection.
The strategic placement of common protecting groups led to the discovery of a new method for "superarming" glycosyl donors. Conceptualized from our previous studies on the O-2/O-5 Cooperative Effect, it was determined that S-benzoxazolyl glycosyl donors possessing both a participating moiety at C-2 and an electronically armed lone pair at O-5, such as the superarmed glycosyl donor shown above, were exceptionally reactive.
Mydock
Laurel K
LK
Department of Chemistry and Biochemistry, University of Missouri-St. Louis, St. Louis, Missouri 63121, USA.
Demchenko
Alexei V
AV
D019817:Benzoic Acid / Q000737:chemistry*; D001583:Benzoxazoles / Q000138:chemical synthesis / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation
D001583:Benzoxazoles; D006027:Glycosides; D019817:Benzoic Acid