Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2018, Issue 20-21, Pages 2701-2706Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201800260
Keywords
Glycosylation; Protecting groups; Diastereoselectivity; Natural products; Neighboring-group effects
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Funding
- Austrian Research Promotion Agency (FFG, BRIDGE-Project) [843488]
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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-,d-glucoside.
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