A STRAIGHTFORWARD ROUTE TO HYDANTOCIDIN ANALOGS WITH PYRANOSE RING STRUCTURE

Authors
OSZ E SOS E SOMSAK L SZILAGYI L DINYA Z
Citation
E. Osz et al., A STRAIGHTFORWARD ROUTE TO HYDANTOCIDIN ANALOGS WITH PYRANOSE RING STRUCTURE, Tetrahedron, 53(16), 1997, pp. 5813-5824
Citations number
37
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
16
Year of publication
1997
Pages
5813 - 5824
Database
ISI
SICI code
0040-4020(1997)53:16<5813:ASRTHA>2.0.ZU;2-W
Abstract
Partial hydrolysis of the nitrile moiety in acetylated 1-bromo-glycopy ranosyl cyanides 1 and 9 mediated by TiCl4 gave C-(1-bromo-1-deoxy-gly copyranosyl)formamides 2 and 10 whose reaction either with AgOCN, AgSC N or KSCN in nitromethane resulted in the formation of glycopyranosyli dene-spirohydantoins 3, 11 and 15 and -thiohydantoins 7 and 16. Zemple n-deacetylation gave the pyranoid epi-hydantocidin analogues 4 and 12, and thiohydantocidin analogues 8 and 17, respectively. (C) 1997 Elsev ier Science Ltd.