Orthogonal cleavage of the 2-naphthylmethyl group in the presence of the p-methoxy phenyl-protected anomeric position and its use in carbohydrate synthesis
Literature Information
Publication Date
2016-04-29
DOI
10.1039/C6QO00144K
Impact Factor
5.281
Authors
Vittorio Cattaneo, Davide Oldrini, Alessio Corrado, Francesco Berti, Roberto Adamo
View Original
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.
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Source Journal
Organic Chemistry Frontiers
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8.7%
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