Superarming the S-Benzoxazolyl Glycosyl Donors by Simple 2-O-Benzoyl-3,4,6-tri-O-benzyl Protection
- 1 May 2008
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 10 (11), 2103-2106
- https://doi.org/10.1021/ol800345j
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.Keywords
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