Chemical Glucosylation of Labile Natural Products Using a (2‐Nitrophenyl)acetyl‐Protected Glucosyl Acetimidate Donor. Issue 20 (26th April 2018)

• Record Type: Journal Article
• Authors: Weber, Julia; Schwarz, Markus; Schiefer, Andrea; Hametner, Christian; Häubl, Georg; Fröhlich, Johannes; Mikula, Hannes
• Is Part Of: European journal of organic chemistry. Issue 20/21(2018)
• Page Start: 2701
• Page End: 2706
• Publication Date: 2018-04-26
• Subjects: Glycosylation -- Protecting groups -- Diastereoselectivity -- Natural products -- Neighboring‐group effects; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.201800260
• Languages: English
• ISSNs: 1434-193X

Abstract

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. Abstract : (2‐Nitrophenyl)acetyl (NPAc)‐protected glucosyl donors have been prepared and investigated towards the chemical glucosylation of natural products. The reductive conditions for deprotection of NPAc‐groups are compatible with many functional groups including ester functionalities and unsaturated carbon–carbon bonds. A glucosylated metabolite of T2‐toxin was synthesized by a convenient "one‐pot" procedure.