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Letters in Organic Chemistry


ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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

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

Volume 5, Issue 7, 2008

Page: [576 - 578] Pages: 3

DOI: 10.2174/157017808785982130

Price: $65


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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