Spirodiketopiperazines at the anomeric position of mannopyranose: Novel N-linked glycopeptides incorporating an α-amino acid at the anomeric position of mannopyranose

Article abstract of DOI:10.1016/0040-4039(95)01732-W

The first synthesis of a spirodiketopiperazine at the anomeric carbon of a pyranose sugar is described; an N-acylated bicyclic amino [2.2.2.] lactone provides access to a new class of glycopeptide analogues of pyranoses and determines the anomeric configuration of the spirodiketopiperazine. The mannopyranose may be equilibrated to the more stable furanose form.