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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
- 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]
- Subjects :
- *MERCURY compounds
*CHEMICAL reactions
*THIOUREA
Subjects
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