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Chemical Glucosylation of Labile Natural Products Using a (2‐Nitrophenyl)acetyl‐Protected Glucosyl Acetimidate Donor
Author(s) -
Weber Julia,
Schwarz Markus,
Schiefer Andrea,
Hametner Christian,
Häubl Georg,
Fröhlich Johannes,
Mikula Hannes
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201800260
Subject(s) - chemistry , hydrogenolysis , glycosylation , glycoside , organic chemistry , total synthesis , combinatorial chemistry , stereochemistry , biochemistry , catalysis
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.