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. 2007 Oct 11;9(21):4115-8.
doi: 10.1021/ol701466u. Epub 2007 Sep 22.

Revisiting the armed-disarmed concept: the importance of anomeric configuration in the activation of S-benzoxazolyl glycosides

David Crich  1 , Ming Li
Affiliations

Revisiting the armed-disarmed concept: the importance of anomeric configuration in the activation of S-benzoxazolyl glycosides

David Crich et al. Org Lett. .

Abstract

The unexpectedly high reactivity of a (2-benzoxazolyl) per-O-benzoyl-beta-D-thioglucoside and related donors in reactions promoted by copper(II) trifluoromethanesulfonate is revealed, by comparison with the unreactive alpha-anomer, to be the result of neighboring group participation. Revision of the armed-disarmed concept for glycosyl donors is not required.

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Figures

Figure 1
Figure 1
Donor reactivity sequence with Cu(OTf)2
Figure 2
Figure 2
Literature examples of the phenomenon
Scheme 1
Scheme 1
Trisaccharide synthesis
Scheme 2
Scheme 2
Synthesis of the α-SBox donor 8
Scheme 3
Scheme 3
Synthesis of the α-SBox donor 13
See this image and copyright information in PMC

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