Issue 6, 2016

Orthogonal cleavage of the 2-naphthylmethyl group in the presence of the p-methoxy phenyl-protected anomeric position and its use in carbohydrate synthesis

Abstract

Orthogonal removal of naphthylmethyl (NAP) and anomeric O-p-methoxyphenyl (PMP) ethers using 2,3-dichloro-5,6-dicyano-1,4-benzoquinone and cerium(IV) ammonium nitrate, respectively, is described. These reactions were tested in the oligosaccharide assembly of biologically relevant motifs, such as α-D-Man-(1,3)-[α-D-(1,6)-Man]-α-D-Man, α-D-Fuc-(1,2)-α-D-Fuc and α-D-NeuNAc-(2,3)-β-D-Gal. The usefulness of these chemoselective deprotections was proven in the synthesis of high mannoses.

Graphical abstract: Orthogonal cleavage of the 2-naphthylmethyl group in the presence of the p-methoxy phenyl-protected anomeric position and its use in carbohydrate synthesis

Supplementary files

Article information

Article type
Research Article
Submitted
06 abr. 2016
Accepted
28 abr. 2016
First published
29 abr. 2016

Org. Chem. Front., 2016,3, 753-758

Orthogonal cleavage of the 2-naphthylmethyl group in the presence of the p-methoxy phenyl-protected anomeric position and its use in carbohydrate synthesis

V. Cattaneo, D. Oldrini, A. Corrado, F. Berti and R. Adamo, Org. Chem. Front., 2016, 3, 753 DOI: 10.1039/C6QO00144K

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