Issue 13, 2015

Synthesis and photosensitivity of isoxazolin-5-one glycosides


A novel procedure for the synthesis of isoxazolin-5-one glycosides starting from unprotected carbohydrates is described. The substrate scope of the one-pot synthetic protocol was explored using D-configured glucose, xylose, maltose, fructose, ribose and 2-deoxyribose. Naturally occurring 2-(β-D-glucopyranosyl)-3-isoxazolin-5-one and four novel isoxazolin-5-one glycosides derived from xylose, maltose and fructose were synthesized and purified by flash chromatography. The compounds were characterized in terms of chemical structure, photophysical properties as well as pH stability. The photohydrolysis rates of the synthesized glycosides were compared with uridine as a standard to determine the quantum yields for the photoreactions in water.

Graphical abstract: Synthesis and photosensitivity of isoxazolin-5-one glycosides

Supplementary files

Article information

Article type
04 Feb 2015
23 Feb 2015
First published
23 Feb 2015
This article is Open Access
Creative Commons BY license

Org. Biomol. Chem., 2015,13, 4025-4030

Author version available

Synthesis and photosensitivity of isoxazolin-5-one glycosides

T. Becker, P. Kartikeya, C. Paetz, S. H. von Reuß and W. Boland, Org. Biomol. Chem., 2015, 13, 4025 DOI: 10.1039/C5OB00244C

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