An efficient synthetic route to O-(2-O-benzyl-3,4-di-O-acetyl-α/β-l-fucopyranosyl)-trichloroacetimidate
Résumé
An efficient synthetic route to prepare O-(2-O-benzyl-3,4-di-O-acetyl-α/β-L-fucopyranosyl)-trichloroacetimidate from L-fucose was developed by introducing the thiophenyl group at the anomeric center and the benzylidene functional group to protect the 3 and 4 positions. Although three approaches were considered, the best result was obtained when, after the 2-hydroxyl benzylation, both protective groups were simultaneously removed by using acetic anhydride and perchloric acid supported on silica as catalyst. Selective deacetylation of the obtained tri-Oacetate followed by the reaction of the resultant hemiacetal with trichloroacetonitrile and DBU afforded the trichloroacetimidate with an overall yield of 56% from the L-fucose.
Domaines
Sciences du Vivant [q-bio]| Origine | Fichiers produits par l'(les) auteur(s) |
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