- cis-Fused bicyclic sugar thiocarbamates. Reactivity towards amines
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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.
- López, óscar,Zafra, Encarnación,Maya, Inés,Fuentes, José,Diánez, Ma Jesús,Estrada, Ma Dolores,Pérez-Garrido, Simeón,Fernández-Bola?os, José G.
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experimental part
p. 11789 - 11796
(2009/04/11)
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- UNPROTECTED SUGAR PHOSPHINIMINES: A FACILE ROUTE TO CYCLIC CARBAMATES OF AMINO SUGARS
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Unprotected sugar phosphinimines were prepared from various azido sugars by reaction with triphenylphosphine and were converted by carbon dioxide into cyclic carbamates of amino sugars.The reaction could be carried out more conveniently in a one-pot process without isolation of the phosphinimines.The 13C- and 31P-n.m.r. data for N-(β-D-glucopyranosyl)triphenylphosphine imide (2) revealed an unexpected conformation of the phosphinimine moiety (proposed as a "reverse exo-anomeric effect") stabilised by an interaction with HO-2.
- Kovacs, Jozsef,Pinter, Istvan,Messmer, Andras,Toth, Gabor
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