Synthesis of Thiadiazolylaminoglycosides Through  Ring Contraction  of Triazinoglycosides Induced by [TBA‐Ox] | Zendy

Kikelj Vincent | Zendy; Julienne Karine | Zendy; Chalopin Thibaut | Zendy; Gouin Sébastien G. | Zendy; Evain Michel | Zendy; Deniaud David | Zendy

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Synthesis of Thiadiazolylaminoglycosides Through Ring Contraction of Triazinoglycosides Induced by [TBA‐Ox]

Author(s) -

Kikelj Vincent,

Julienne Karine,

Chalopin Thibaut,

Gouin Sébastien G.,

Evain Michel,

Deniaud David

Publication year - 2015

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.2232

Subject(s) - chemistry , contraction (grammar) , ring (chemistry) , stereochemistry , formic acid , organic chemistry , medicine

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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