Synthesis of a Phosphonate Analog of Sialic Acid (Neu5Ac) Using Indium-Mediated Allylation of Unprotected Carbohydrates in Aqueous Media

摘要

This paper summarizes a short synthesis of a phosphonate analog 3 of sialic acid (1, 50% yield based on consumed N-acetyl-β-D-mannosamine (5)). Compound 3 may be useful in studying a number of aspects of the glycobiology of sialic acid: for example, for the syntheses of phosphonate analogs of gangliosides or sialyl Lewis x; for the preparation of C-glycosides of the phosphonate analog of sialic acid; as a basis for phosphonate-based probes to study sialic acid—receptor interactions by ~(31)P NMR analysis; and as isosteres for sialic acid to study the influence of charge—charge interactions on the binding of derivatives of sialic acid to their receptors.