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On the mechanism of formation of glycofurano[2,1-d]-imidazolidin-2-ones. Reaction of 2-amino-2-deoxyheptopyranoses with isocyanates.

✍ Scribed by Martin Avalos; Reyes Babiano; Pedro Cintas; José L. Jiménez; Juan C. Palacios; Concepción Valencia

Book ID
104203916
Publisher
Elsevier Science
Year
1993
Tongue
French
Weight
971 KB
Volume
49
Category
Article
ISSN
0040-4020

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✦ Synopsis

Reaction of 2-ammosugars with isocyanates has been extended to other higher-carbon sugars. Ureido derivat~es or, in most cams. monocychc struc~es can be easily isolated Importantly, the last substances display a relative rrons disposition between the substituents at C-4 and C-5 of the heterocyclic ring, as a consequence of a rapId cis-fruns isomerisation in acids media. 'IIns sbeoche.mical feature ensures the stereocontrolled ring closure to give exclusively crs-fused glycofmanose systems. In the light of these results, some related reactions have been revised.

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