Superarming the S-benzoxazolyl glycosyl donors by simple 2-O-benzoyl-3,4,6-tri-O-benzyl protection |
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Authors: | Mydock Laurel K Demchenko Alexei V |
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Affiliation: | Department of Chemistry and Biochemistry, University of Missouri-St. Louis, St. Louis, Missouri 63121, USA. |
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Abstract: | 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. |
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