Indirect synthetic route to α-l-fucosides via highly stereoselective construction of α-l-galactosides followed by C6-deoxygenation.

We developed an indirect synthetic method for α-l-fucosides. Based on the fact that l-fucose is 6-deoxy-l-galactose, our strategy consists of the stereoselective construction of α-l-galactoside and its conversion to α-l-fucoside via C6-deoxygenation. The formation of α-l-galactoside is strongly directed using 4,6-O-di-tert-butylsilylene(DTBS)-protected l-galactosyl donors. The DTBS-directed α-l-galactosylation showed broad substrate applicability along with excellent coupling yield and α-selectivity. In the C6-deoxygenation of α-l-galactosides, the Barton-McCombie reaction facilitated the conversion to l-fucosides with good yield. To demonstrate the applicability of our method, we synthesized naturally occurring α-l-fucosides.

Citation

Hirotaka Tomida, Takuya Matsuhashi, Hide-Nori Tanaka, Naoko Komura, Hiromune Ando, Akihiro Imamura, Hideharu Ishida. Indirect synthetic route to α-l-fucosides via highly stereoselective construction of α-l-galactosides followed by C6-deoxygenation. Organic & biomolecular chemistry. 2020 Jul 08;18(26):5017-5033

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PMID: 32573638

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