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

An efficient synthetic route to O-(2-O-benzyl-3,4-di-O-acetyl-α/β-l-fucopyranosyl)-trichloroacetimidate.
Carbohydr Res. 2020 Dec 18;:108221
Authors: Tolón Murguía BI, Iglesias Morales YLM, Mesa Hernández M, Yu Pérez Y, Labrada Regalado C, Garrido Arteaga R, Paquet F, López López MA
Abstract
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-O-acetate 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.
PMID: 33358524 [PubMed - as supplied by publisher]

Source: Carbohydrate Research - December 18, 2020 Category: Genetics & Stem Cells Authors: Tolón Murguía BI, Iglesias Morales YLM, Mesa Hernández M, Yu Pérez Y, Labrada Regalado C, Garrido Arteaga R, Paquet F, López López MA Tags: Carbohydr Res Source Type: research