Synthesis of C-disaccharides via a hetero-Diels–Alder reaction and further stereocontrolled transformations

The partial de novo synthesis of two new C-disaccharides containing d-glucosamine is described. The strategy is based on a hetero-Diels–Alder reaction leading to a 1:1 mixture of separable cycloadducts, which have been stereoselectively functionalized and converted into α-d-Galp-(1→3)-C-d-GlcpNAc and α-l-Galp-(1→3)-C-d-GlcpNAc.

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