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Samarium Diiodide Mediated Coupling of Glycosyl Phosphates with Carbon Radical or Anion Acceptors—Synthesis of C‐Glycosides
Author(s) -
Hung ShangCheng,
Wong ChiHuey
Publication year - 1996
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199626711
Subject(s) - glycosyl , chemistry , samarium diiodide , ion , carbohydrate , coupling reaction , glycoside , carbon fibers , samarium , combinatorial chemistry , organic chemistry , photochemistry , catalysis , materials science , composite number , composite material
Carbohydrate mimetics for the study of carbohydrate recognition in biological systems can be C‐glycosides, which can now be prepared by the SmI 2 ‐mediated coupling of glycosyl phosphates with carbon radical or carbon anion acceptors. The reaction proceeds by one‐electron processes via the radical or the anion, respectively (see scheme on the right), and is complete within 15–30 min.