β-Selective one-pot fluorophosphorylation of d,d -heptosylglycals mediated by selectfluor

Research output: Contribution to journalArticle

Abstract

This study describes the development of a novel procedure of glycal fluorophosphorylation applied to the synthesis of a fluorinated analogue of an important bacterial metabolite. This procedure was applied to several heptose-derived glycals, and the stereochemical outcome of the reaction was analyzed. Under optimized conditions, the reaction is β-gluco selective, but a significant amount of the α-gluco diastereomer is also generated.

Original languageEnglish
Pages (from-to)392-397
Number of pages6
JournalIsrael journal of chemistry
Volume55
Issue number3-4
DOIs
Publication statusPublished - 1 Apr 2015

Fingerprint

Heptoses
Metabolites
selectfluor

Keywords

  • antibiotics
  • fluorosugars
  • LPS
  • phosphorylation
  • Selectfluor

Cite this

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abstract = "This study describes the development of a novel procedure of glycal fluorophosphorylation applied to the synthesis of a fluorinated analogue of an important bacterial metabolite. This procedure was applied to several heptose-derived glycals, and the stereochemical outcome of the reaction was analyzed. Under optimized conditions, the reaction is β-gluco selective, but a significant amount of the α-gluco diastereomer is also generated.",
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β-Selective one-pot fluorophosphorylation of d,d -heptosylglycals mediated by selectfluor. / Vincent, Stéphane; Tikad, Abdellatif.

In: Israel journal of chemistry, Vol. 55, No. 3-4, 01.04.2015, p. 392-397.

Research output: Contribution to journalArticle

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