Stereoselective Synthesis of 5-Thio-β-L-Fucopyranosyl Phosphate

Tatsuo      Miyazaki; Daisuke      Hiyoshi; Masayuki      Izumi; Hironobu      Hashimoto; Hideya      Yuasa

doi:10.2174/157017808785982130

Abstract

The fucosyltransferase-catalyzed 5-thiofucosylation reaction suffered from limitations in the β-selective synthesis of GDP-5-thiofucose, a donor substrate. We found that the use of electronegatively-substituted benzoate groups for 5-thiofucose protection improved the β-selectivity in the phosphorylation step. We thus achieved the synthesis of 5-thio-β- L-fucosyl phosphate in 50% yield from 5-thiofucose, using the 3,5-dinitrobenzoyl group.

Keywords: 5-thiofucose, phosphorylation, glycosyl phosphate, stereoselectivity

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Letters in Organic Chemistry

Title: Stereoselective Synthesis of 5-Thio-β-L-Fucopyranosyl Phosphate

Volume: 5 Issue: 7

Author(s): Tatsuo Miyazaki, Daisuke Hiyoshi, Masayuki Izumi, Hironobu Hashimoto and Hideya Yuasa

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Keywords: 5-thiofucose, phosphorylation, glycosyl phosphate, stereoselectivity

Abstract: The fucosyltransferase-catalyzed 5-thiofucosylation reaction suffered from limitations in the β-selective synthesis of GDP-5-thiofucose, a donor substrate. We found that the use of electronegatively-substituted benzoate groups for 5-thiofucose protection improved the β-selectivity in the phosphorylation step. We thus achieved the synthesis of 5-thio-β- L-fucosyl phosphate in 50% yield from 5-thiofucose, using the 3,5-dinitrobenzoyl group.

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Miyazaki Tatsuo, Hiyoshi Daisuke, Izumi Masayuki, Hashimoto Hironobu and Yuasa Hideya, Stereoselective Synthesis of 5-Thio-β-L-Fucopyranosyl Phosphate, Letters in Organic Chemistry 2008; 5 (7) . https://dx.doi.org/10.2174/157017808785982130