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Simple and efficient synthesis of O-unprotected glycosyl thiourea and isourea derivatives from glycosylamines

Simple and efficient synthesis of O-unprotected glycosyl thiourea and isourea derivatives from glycosylamines

Authors :
López, Óscar
Maya, Inés
Fuentes, José
Fernández-Bolaños, José G.
Source :
Tetrahedron. Jan2004, Vol. 60 Issue 1, p65. 12p.
Publication Year :
2004

Abstract

Practical, facile and high-yielding one-pot syntheses of different O-unprotected glycopyranosyl thioureas and thioureido bolaamphiphiles (two-step synthesis) and of 2-amino-4,5-dihydro-(1,2-dideoxy-β-d-glucopyranoso)[1,2-d]oxazoles (three-step synthesis) from glycopyranosylamines are reported. The method involves the preparation of O-unprotected β-d-gluco (and d-galacto)pyranosyl isothiocyanates which are in equilibrium with the corresponding 1,2-cyclic thiocarbamates, coupling with amines to afford glycosyl thioureas and treatment with yellow mercury (II) oxide to give trans-fused bicyclic isoureas. A d-gluco trehazolin analogue is prepared in this way. In situ transformation of N,N-dialkyl, N′-glucopyranosyl thioureas into the corresponding ureas is also reported. [Copyright &y& Elsevier]

Details

Language :
English
ISSN :
00404020
Volume :
60
Issue :
1
Database :
Academic Search Index
Journal :
Tetrahedron
Publication Type :
Academic Journal
Accession number :
11609218
Full Text :
https://doi.org/10.1016/j.tet.2003.10.092