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. 2012:8:597-605.
doi: 10.3762/bjoc.8.66. Epub 2012 Apr 18.

2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis

Hemali D Premathilake  1 , Alexei V Demchenko
Affiliations

2-Allylphenyl glycosides as complementary building blocks for oligosaccharide and glycoconjugate synthesis

Hemali D Premathilake et al. Beilstein J Org Chem. 2012.

Abstract

The O-allylphenyl (AP) anomeric moiety was investigated as a new leaving group that can be activated for chemical glycosylation under a variety of conditions, through both direct and remote pathways. Differentiation between the two activation pathways was achieved in a mechanistic study. The orthogonal-type activation of the AP moiety along with common thioglycosides allows for the execution of efficient oligosaccharide assembly.

Keywords: carbohydrates; glycosylation; leaving group; oligosaccharides; orthogonal strategy; selective activation.

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Figures

Scheme 1
Scheme 1
Orthogonal strategy introduced by Ogawa et al.
Scheme 2
Scheme 2
Determination of the AP activation pathways.
Scheme 3
Scheme 3
AP building blocks in oligosaccharide synthesis.
See this image and copyright information in PMC

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