cis-Fused bicyclic sugar thiocarbamates. Reactivity towards amines |
| |
Authors: | Ó scar Ló pez,Iné s Maya,Ma Jesú s Diá nez,Simeó n Pé rez-Garrido |
| |
Affiliation: | a Departamento de Química Orgánica, Facultad de Química, Universidad de Sevilla, P.O. Box 1203, E-41071 Sevilla, Spain b Instituto de Ciencias de Materiales de Sevilla and Departamento de Física de la Materia Condensada, CSIC-Universidad de Sevilla, P.O. Box 1065, E-41071 Sevilla, Spain |
| |
Abstract: | 1,2-cis-Fused bicyclic sugar thiocarbamates of gluco and manno configurations have been prepared by treatment of the corresponding O-unprotected amino sugars and glycopyranosyl amines with thiophosgene. The reactivity of these compounds towards amines has been studied in order to determine whether these compounds could act as latent isothiocyanates; it is shown that 1,2-cis-fused bicyclic sugar thiocarbamates are more stable than their trans analogues, and are not transformed into thioureas upon treatment with amines. An unprecedented isomerization of a peracetylated glucopyranoso[2,1-d]oxazolidine-2-thione into a glucopyranoso[2,1-d]thiazolidin-2-one in DMF is also reported. The structure of this thiazolidin-2-one was confirmed by X-ray crystallography. |
| |
Keywords: | Thiophosgene Thiocarbamates Carbamates Annelation Amino sugars |
本文献已被 ScienceDirect 等数据库收录! |
|