132591-23-2Relevant academic research and scientific papers
Synthesis of C-Glycosides of N-Acetylneuraminic Acid and Other Derivatives
Paulsen, Hans,Matschulat, Peter
, p. 487 - 495 (2007/10/02)
Reaction of the β-pyranosyl chloride 1 of N-acetylneuraminic acid with allyl(tributyl)stannane under radical-induced conditions affords a mixture of the allyl C-glycosides 2/3.After deprotection, the pure allyl α-C-glycoside 5 and the analogous β isomer 7 can be isolated.The allyl C-glycosides 2 and 3 are converted into the corresponding epoxypropyl C-glycosides 9 and 11 by epoxidation of the allylic group.Further modified allyl C-glycosides are prepared from the C-3-hydroxylated N-acetylneuraminic acid, which are available as pure α- and β-glycosides 19 and 21 after deprotection.At C-3 modified compounds are also synthesized which have allyl and azido residues at C-3.All compounds are interesting as potential inhibitors of sialidases, CMP sialate syntheses, and viral infection.
