Synthesis of new sugar amino acid derivatives of D-glucosamine.
The synthesis of several new sugar amino acid derivatives of 2-acetamido-2-deoxy-D-glucose, bearing a C-glycosyl functionality as building blocks for the design and synthesis of natural glycoconjugates mimetics, is described. These compounds were prepared from the readily accessible per-benzylated amino C-allyl glucopyranosyl compounds, with TMSOTf/Ac(2)O-mediated selective acetolysis of the 6-O-benzyl group as the key step.
Xie
Juan
J
Laboratoire de Chimie des Glucides, CNRS UMR 7613, Université Pierre et Marie Curie, 4 Place Jussieu, F-75005, Paris, France. xie@ccr.jussieu.fr
D000117:Acetylglucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis; D000596:Amino Acids / Q000138:chemical synthesis*; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D000596:Amino Acids; D005944:Glucosamine; D000117:Acetylglucosamine