352437-48-0Relevant academic research and scientific papers
5-azido derivatives of neuraminic acid - Synthesis and structure
Schneider, Regine,Freyhardt, Clemens C.,Schmidt, Richard R.
, p. 1655 - 1661 (2007/10/03)
Benzyl sialoside 1 was transformed into the corresponding 5-azido derivative 4 by N-nitrosation of the 5-acetylamino group and treatment with base followed by hydrazoic acid or, alternatively, by N,O-deacetylation followed by diazo group transfer to the amino moiety by means of TfN3. Regioselective 4-O-acetylation and introduction of the MPM group at 9-O afforded glycosyl acceptor 11. N,O-Deacetylation of ethyl 2-thiosialoside 13 afforded 14 which, after diazo group transfer to the amino group, furnished 5-azido derivative 16, which can serve as a sialyl donor. Activation of the ethylthio leaving group in the absence of an acceptor afforded 2,3-dehydro derivative 17. Regioselective 4-O-acetylation and 9-O-benzylation furnished glycosyl acceptor 22. An X-ray analysis was obtained from crystals of the 7,8,9-O-unprotected intermediate 21.
