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. 2013 Sep 20;15(18):4904-7.
doi: 10.1021/ol402371b. Epub 2013 Sep 5.

Superarming of glycosyl donors by combined neighboring and conformational effects

Mads Heuckendorff  1 , Hemali D Premathilake, Papapida Pornsuriyasak, Anders Ø Madsen, Christian M Pedersen, Mikael Bols, Alexei V Demchenko
Affiliations

Superarming of glycosyl donors by combined neighboring and conformational effects

Mads Heuckendorff et al. Org Lett. .

Abstract

A novel glycosyl donor that combines the concepts of both conformational and electronic superarming has been synthesized. The reactivity and selectivity of the donor have been tested in competition experiments.

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Figures

Figure 1
Figure 1
Crystal structure of 1a.
Scheme 1
Scheme 1
Chemoselective strategies for oligosaccharide synthesis: A. Armed-disarmed; B. Conformational superarming; C. Electronic superarming.
Scheme 2
Scheme 2
Competition experiment between conformationally superarmed donor 1a and electronically superarmed donor 1b.
Scheme 3
Scheme 3
Competition experiment between the hybrid donor 1c and previously developed donors 1a and 1b.
Scheme 4
Scheme 4
Competition experiment between donor 1c and donor 1e and donor 1f.
See this image and copyright information in PMC

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