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Expedient Synthesis Of Aminooxylated-carbohydrates For Chemoselective Access Of Glycoconjugates

O. Renaudet, P. Dumy
Published 2001 · Chemistry

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Abstract Herein, we describe an efficient preparation of various biologically important carbohydrate motifs bearing an aminooxy group at the anomeric position. These nucleophilic sugar analogues represent useful intermediates for the chemoselective preparation of glycoconjugates. The key glycosylation step involves the coupling of fluoro-activated protected sugar and N -hydroxyphthalimide in the presence of BF 3 ·Et 2 O. Final deprotection and cleavage of the phthalimide moiety with methylhydrazine afforded new Glc-β-ONH 2 3 , GalNAc-β-ONH 2 9 , Glc-α-ONH 2 14 , Gal-α-ONH 2 17 and Man-α-ONH 2 20 derivatives with good yields. Compared to the literature results, the preparation of Gal-β-ONH 2 6 , GalNAc-α-ONH 2 11 and Lac-β-ONH 2 23 proved to be more efficient.
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