Synthesis of Thiadiazolylaminoglycosides Through Ring Contraction of Triazinoglycosides Induced by [TBA‐Ox] |
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| Authors: | Vincent Kikelj Karine Julienne Thibaut Chalopin Sébastien G. Gouin Michel Evain David Deniaud |
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| Affiliation: | 1. LUNAM Université, CEISAM, Chimie Et Interdisciplinarité, Synthèse, Analyse, Modélisation, UMR CNRS 6230, UFR des Sciences et des Techniques, 2, rue de la Houssinière, Nantes, France;2. LUNAM Université, Institut des Matériaux Jean Rouxel, UMR CNRS 6502, 2 rue de la Houssinière, Nantes, France |
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| Abstract: | A new synthetic route to thiadiazolylaminoglycosides, by a ring expansion/ring contraction sequence of glycosyl triazines, has been developed. Two potential mechanisms of this oxidative ring contraction using [TBA‐Ox] are discussed. The more plausible involves formation of an oxatriazepane intermediate followed by loss of formic acid, ring opening, and subsequent recyclization. |
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