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

Stéphane Vincent; Abdellatif Tikad

doi:10.1002/ijch.201400148

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

Stéphane Vincent, Abdellatif Tikad

Unite de recherche en chimie organique

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

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.

langue originale	Anglais
Pages (de - à)	392-397
Nombre de pages	6
journal	Israel journal of chemistry
Volume	55
Numéro de publication	3-4
Les DOIs	https://doi.org/10.1002/ijch.201400148
Etat de la publication	Publié - 1 avr. 2015

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10.1002/ijch.201400148

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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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N2 - 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.

AB - 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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KW - fluorosugars

KW - LPS

KW - phosphorylation

KW - Selectfluor

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

Résumé

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