Synthesis and utility of 2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl bromide as a novel α-D-talosaminide building block

Article abstract of DOI:10.1248/cpb.44.15

A novel α-D-talosaminyl donor, 2-(benzoyloxyimino)-2-deoxy-α-D-lyxo-hexopyranosyl bromide has been synthesized in a total yield of 32% over 6 steps from D-galactose. The utility of the donor was evaluated for the elaboration of α-D-TalNAc-(1→6)-α-D-Gal, α-D-TalNAc-(1→6)-α-D-Glc, and α-D-TalNAc-(1→3)-L-serine derivatives by a simple 3-step sequence, comprising α-selective glycosylation of appropriately protected acceptors of D-galactose, D-glucose, and L-serine, talo-selective hydroboration of the oxyimino function to an amino group, and N-acetylation.

Full text of DOI:10.1248/cpb.44.15

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NII-Electronic Library Service