Résumé
An efficient multigram-scale synthesis of methyl 2,3,4,6-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside from methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside is reported. It involves a sequence of Swern oxidation, Grignard addition and Fleming-Tamao reactions. The resulting scaffold was used as a precursor to design a small library of clickable L-heptosides. This study shows that the use of mercuric bistrifluoroacetate is required both to accelerate and to cleanly perform the Fleming-Tamao oxidation, without side-reactions.
langue originale | Anglais |
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Pages (de - à) | 71-75 |
Nombre de pages | 5 |
journal | Carbohydrate Research |
Volume | 432 |
Les DOIs | |
Etat de la publication | Publié - 2 sept. 2016 |
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