Tetrahedron p. 5813 - 5824 (1997)
Update date:2022-08-03
Topics:
Osz, Erzsebet
Sos, Erzsebet
Somsak, Laszlo
Szilagyi, Laszlo
Dinya, Zoltan
Partial hydrolysis of the nitrile moiety in aeetylated 1-bromo-glycopyranosyl cyanides 1 and 9 mediated by TiCl4 gave C-(1-bromo-1-deoxy-glycopyranosyl) formamides 2 and 10 whose reaction either with AgOCN, AgSCN or KSCN in nitromethane resulted in the formation of glycopyranosylidene-spirohydantoins 3, 11 and 15 and -thiohydantoins 7 and 16. Zemplen-deacetylation gave the pyranoid epihydantocidin analogues 4 and 12, and thiohydantocidin analogues 8 and 17, respectively.
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