Novel Method for the Synthesis of Cholesteryl Glucosides starting from Disaccharides |
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| Authors: | Stephanie Weiss Philipp M. Neu Christopher Ludwig Sigurd Schober Martin Mittelbach |
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| Affiliation: | 1. Institute of Chemistry, NAWI Graz, University of Graz, 8010 Graz, Austria;2. Competence Centre for Wood Composites and Wood Chemistry (Wood?K Plus), 9300 St. Veit/Glan, Austria |
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| Abstract: | Steryl glucosides (SG) and acylated steryl glucosides (ASG) are natural components of plant cell membranes and present in different concentrations in various plant foods. Currently, their positive effects on human health are under investigation. The present work presents a new and efficient synthesis method for cholesteryl glucosides starting from disaccharides. A five‐step synthesis protocol is done to obtain the desired product in 35% overall yield. In the first step, the hydroxy groups of the starting material sucrose are protected using benzyl ethers. After the subsequent acidic hydrolysis the obtained pyranosyl moiety of the disaccharide is transformed to its trichloroacetimidate derivative. Next, the formation of the glycosidic bond to cholesterol is performed and catalytic transfer hydrogenation in order to remove the protecting groups leads to the desired product. In this context, APCI‐MS‐TOF has turned out to be an excellent analytical tool for the high sensitive analysis of SG as well as intermediates. Practical Applications: Due to the comparatively high amounts of SG and ASG in seeds and oils, not only the food industry but also in biodiesel production, these natural compounds are of increasing interest. However, analysis of the compounds is difficult, commercially available pure standard materials are costly and their synthesis often requires time‐consuming work‐up procedures. The described preparation method allows the synthesis of cholesteryl glucosides which can be used as reference or standard material for the quantitative analysis of phytosteryl glucosides in plant derived samples. The general synthesis method could be also applied to other SG and ASG derivatives.  Cholesteryl glucosides are synthesized using a new and efficient five‐step synthesis protocol starting from disaccharides. The preparation method provides products with good overall yield and high purity and, therefore, the synthesized glucosides can be used as reference or standard material for the quantitative analysis of phytosteryl glucosides in plant derived samples. APCI‐MS‐TOF is extensively used as analytical tool for the sensitive analysis of cholesteryl glucosides as well as intermediates. |
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| Keywords: | benzylation biodiesel contaminants glycosylation phytosterols steryl glucosides |
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Cholesteryl glucosides are synthesized using a new and efficient five‐step synthesis protocol starting from disaccharides. The preparation method provides products with good overall yield and high purity and, therefore, the synthesized glucosides can be used as reference or standard material for the quantitative analysis of phytosteryl glucosides in plant derived samples. APCI‐MS‐TOF is extensively used as analytical tool for the sensitive analysis of cholesteryl glucosides as well as intermediates.