cis-Fused bicyclic sugar thiocarbamates. Reactivity towards amines

• Published in: Tetrahedron Vol. 64; no. 51; pp. 11789 - 11796
• Main Authors: López, Óscar, Zafra, Encarnación, Maya, Inés, Fuentes, José, Diánez, M a Jesús, Estrada, M a Dolores, Pérez-Garrido, Simeón, Fernández-Bolaños, José G.
• Format: Journal Article
• Language: English
• Published: Elsevier Ltd 15-12-2008
• Subjects: Amino sugars; Annelation; Carbamates; Thiocarbamates; Thiophosgene; Carbamates; Annelation; Thiophosgene; Amino sugars; Thiocarbamates
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2008.09.093

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.
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