83956-02-9Relevant academic research and scientific papers
Glycosyl Azides as Starting Materials for the Synthesis of Nucleoside Analogues, 2. - Synthesis of Tetrazole Nucleosides
Zbiral, Erich,Schoerkhuber, Wolfgang
, p. 1870 - 1890 (2007/10/02)
The β-D-ribofuranosyl azide derivative 1 as well as the corresponding α-anomeric compound 3 yield via Staudinger reaction the same P-N-ylide 2.Treatment with alkyl isocyanates RNCO affords the diastereomeric carbodiimide derivatives 5 which can be transformed by HN3 regioselectively into the 1-(β-ribofuranosyl)-5-(alkylamino)tetrazole derivatives 6.Partial or total removal of the protecting groups affords the products 7a, c, d, and 7d'-d'''.The β-D-mannofuranosyl azide derivative 8 is converted via the P-N-ylide 9 into the carbodiimide 10 and the aminotetrazole derivative 11.The reaction of 2 with phenyl isocyanate yields the 5--1-phenyltetrazoles 18 and 19 passing the carbodiimide intermediates 12 and 13.Additionally the 1-isocyanato sugar derivatives 14 and 15 arise which provide for the formation of the products 16, 17, and 20-22.The ethylacetate 23 is formed by reaction of 2 with the azide of monoethyl malonate.The preparation of the ribosyltetrazole derivatives 26 and 27 can be achieved only by preceding synthesis of the syn/anti mixture 24a/24a originating from 2 and acetyl cyanide followed by treatment with HN3.The α-ribosyliminonitrile 25 is assumed to be an intermediate.
