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Journal Article

O-glycoside synthesis with glycosyl iodides under neutral conditions in 1 M LiClO4 in CH2Cl2

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http://pubman.mpdl.mpg.de/cone/persons/resource/persons98735

Waldmann,  Herbert
Abt. IV: Chemische Biologie, Max Planck Institute of Molecular Physiology, Max Planck Society;

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Citation

Schmid, U., & Waldmann, H. (1997). O-glycoside synthesis with glycosyl iodides under neutral conditions in 1 M LiClO4 in CH2Cl2. LIEBIGS ANNALEN-RECUEIL, (12), 2573-2577.


Cite as: http://hdl.handle.net/11858/00-001M-0000-0014-9CB7-8
Abstract
Glycosyl phosphates, imidates, trifluoroacetates, chlorides, and bromides are converted into the respective glycosyl iodides by treatment with LiI or NaI in 1 M solutions of LiClO4 in CH2Cl2. Under these neutral conditions the reactive glycosyl iodides are activated, and react with different glycosyl acceptors to give O-glycosides in moderate yields, with the alpha-anomers predominating. The glycosylation reactions most probably proceed by the initial formation of beta-configured glycosyl iodides from the alpha-configured precursors, and subsequent attack of the glycosyl acceptor on the equatorial iodide from the axial direction.