An unexpected rearrangement giving a new thiosubstituted carbohydrate.
A new thiosubstituted 'd-arabino'-type derivative was obtained from an open carbohydrate via a cascade of four consecutive transformations in a single reaction process. Molecular orbital computations were also performed to explain the stereochemical outcome of the reaction.
Martinez
Agathe
A
Institut de Chimie Moléculaire de Reims, UMR CNRS, Université de Reims, Reims Cedex, France.
Hénon
Eric
E
Coiffier
Claire
C
Banchet
Aline
A
Harakat
Dominique
D
Nuzillard
Jean-Marc
JM
Haudrechy
Arnaud
A
D000447:Aldehydes / Q000737:chemistry; D002241:Carbohydrates / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D011789:Quantum Theory; D013237:Stereoisomerism; D013455:Sulfur / Q000737:chemistry*
D000447:Aldehydes; D002241:Carbohydrates; D013455:Sulfur