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Issue 26, 2020
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Indirect synthetic route to α-l-fucosides via highly stereoselective construction of α-l-galactosides followed by C6-deoxygenation

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Abstract

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.

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

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Supplementary files

Article information


Submitted
01 Jun 2020
Accepted
17 Jun 2020
First published
18 Jun 2020

Org. Biomol. Chem., 2020,18, 5017-5033
Article type
Research Article

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

H. Tomida, T. Matsuhashi, H. Tanaka, N. Komura, H. Ando, A. Imamura and H. Ishida, Org. Biomol. Chem., 2020, 18, 5017
DOI: 10.1039/D0OB01128B

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