An efficient synthetic route to O-(2-O-benzyl-3,4-di-O-acetyl-α/β-l-fucopyranosyl)-trichloroacetimidate

Blanca I Tolón Murguía (1) , Yuleidys de Las Mercedes Iglesias Morales (1) , Miriam Mesa Hernández (1) , Yaneisy Yu Pérez (1) , Claudia Labrada Regalado (1) , Raine Garrido Arteaga (1) , Françoise Paquet (2) , Miguel A López López (1)

1 Finlay Institute of Vaccines
2 CBM - Centre de biophysique moléculaire

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.

Mots clés: Benzylidene; Thiophenyl; Trichloroacetimidate; l-fucose

Domaines: Sciences du Vivant [q-bio]

Blanca I Tolón Murguía, Yuleidys de Las Mercedes Iglesias Morales, Miriam Mesa Hernández, Yaneisy Yu Pérez, Claudia Labrada Regalado, et al.. An efficient synthetic route to O-(2-O-benzyl-3,4-di-O-acetyl-α/β-l-fucopyranosyl)-trichloroacetimidate. Carbohydrate Research, 2020, 499, ⟨10.1016/j.carres.2020.108221⟩. ⟨hal-03432512⟩