Record link: 
http://hdl.handle.net/20.500.12708/144987
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Title: 
Chemical Glucosylation of Labile Natural Products using a (2‐Nitrophenyl)acetyl‐Protected Glucosyl Acetimidate Donor
en
Citation: 
Weber, J., Schwarz, M., Schiefer, A., Hametner, C., Häubl, G., Fröhlich, J., & Mikula, H. (2018). Chemical Glucosylation of Labile Natural Products using a (2‐Nitrophenyl)acetyl‐Protected Glucosyl Acetimidate Donor. European Journal of Organic Chemistry, 2018(20–21), 2701–2706. https://doi.org/10.1002/ejoc.201800260
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Publisher DOI: 
10.1002/ejoc.201800260
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Publication Type: 
Article - Original Research Article
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Language: 
English
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Authors: 
Weber, Julia 
Schwarz, Markus 
Schiefer, Andrea 
Hametner, Christian 
Häubl, Georg 
Fröhlich, Johannes 
Mikula, Hannes 
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Organisational Unit: 
E163-03-2 - Forschungsgruppe Molekulare Chemie und Chemische Biologie 
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Journal: 
European Journal of Organic Chemistry 
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ISSN: 
1434-193X
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Date (published): 
2018
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Number of Pages: 
6
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Publisher: 
WILEY-V C H VERLAG GMBH
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Peer reviewed: 
Yes
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Keywords: 
Physical and Theoretical Chemistry; Organic Chemistry
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Abstract: 
The synthesis of (2-nitrophenyl)acetyl (NPAc)-protected glucosyl donors is described that were designed for the neighboring-group assisted glucosylation of base-labile natural products also being sensitive to hydrogenolysis. Glycosylation conditions were optimized using a trichloroacetimidate glucosyl donor, and cyclohexylmethanol and (+)-menthol as model acceptors. The approach was then extended to a one-pot procedure for the synthesis of 1,2-trans-glycosides. This method was finally applied for improved synthesis of the masked mycotoxin T2-O-β,d-glucoside.
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Research Areas: 
außerhalb der gesamtuniversitären Forschungsschwerpunkte: 100%
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Science Branch: 
Chemie
Biologie
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