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Issue 29, 2013
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Orthogonally protected d-galactosamine thioglycoside building blocks via highly regioselective, double serial and double parallel inversions of β-d-thiomannoside

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Abstract

An efficient route for the synthesis of orthogonally protected D-galactosamine thioglycosides via one-pot double serial and double parallel displacements of the D-mannosyl-2,4-bis-trifluoromethanesulfonates by azide and nitrite ions is described. These building blocks were utilized to synthesize the rare disaccharide moiety of the zwitterionic polysaccharide of Bacteroides fragilis and the selectively protected Tn antigen.

Graphical abstract: Orthogonally protected d-galactosamine thioglycoside building blocks via highly regioselective, double serial and double parallel inversions of β-d-thiomannoside

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Article information


Submitted
03 May 2013
Accepted
28 May 2013
First published
29 May 2013

Org. Biomol. Chem., 2013,11, 4825-4830
Article type
Paper

Orthogonally protected D-galactosamine thioglycoside building blocks via highly regioselective, double serial and double parallel inversions of β-D-thiomannoside

M. Emmadi and S. S. Kulkarni, Org. Biomol. Chem., 2013, 11, 4825
DOI: 10.1039/C3OB40935J

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