Synthesis 2019; 51(12): 2484-2488
DOI: 10.1055/s-0037-1611800
psp
© Georg Thieme Verlag Stuttgart · New York

Practical Gram-Scale Synthesis of Either α- or β-Anomer of C-Vinyl Glycosides

Florian Rouzier
a  IMMM - UMR 6283 CNRS, Le Mans Université, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France   Email: stephane.guillarme@univ-lemans.fr
,
Rosanne Sillé
a  IMMM - UMR 6283 CNRS, Le Mans Université, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France   Email: stephane.guillarme@univ-lemans.fr
,
Arnaud Nourry
a  IMMM - UMR 6283 CNRS, Le Mans Université, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France   Email: stephane.guillarme@univ-lemans.fr
,
Arnaud Tessier
b  CEISAM, UMR 6220 CNRS, Université de Nantes, Faculté des Sciences et des Techniques, 2, rue de la Houssinière, 44322 Nantes cedex 3, France
,
Muriel Pipelier
b  CEISAM, UMR 6220 CNRS, Université de Nantes, Faculté des Sciences et des Techniques, 2, rue de la Houssinière, 44322 Nantes cedex 3, France
,
Stéphane Guillarme*
a  IMMM - UMR 6283 CNRS, Le Mans Université, Avenue Olivier Messiaen, 72085 Le Mans, Cedex 9, France   Email: stephane.guillarme@univ-lemans.fr
› Author Affiliations
This work was supported by the Région des Pays de la Loire through the GlycoOuest program and the Ministère de l’Enseignement Supérieur et de la Recherche of France [Ph.D. fellowship (F.R.)].
Further Information

Publication History

Received: 15 February 2019

Accepted after revision: 22 March 2019

Publication Date:
15 April 2019 (eFirst)

Abstract

The synthesis C-vinyl glycosides, useful intermediates for the synthesis of C-glycoconjugates, was carried out on gram-scale by controlled reduction of the corresponding ethynyl derivatives in good to excellent yields in different carbohydrate series.

Supporting Information

 
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