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O ‐Glycoside Synthesis with Glycosyl Iodides under Neutral Conditions in 1 M LiClO 4 in CH 2 Cl 2
Author(s) -
Schmid Uschi,
Waldmann Herbert
Publication year - 1997
Publication title -
liebigs annalen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0947-3440
DOI - 10.1002/jlac.199719971223
Subject(s) - glycosyl , chemistry , iodide , glycosylation , glycoside , anomer , acceptor , glycosyl donor , medicinal chemistry , organic chemistry , biochemistry , physics , condensed matter physics
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 LiClO 4 in CH 2 Cl 2 . 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 α‐anomers predominating. The glycosylation reactions most probably proceed by the initial formation of β‐configured glycosyl iodides from the α‐configured precursors, and subsequent attack of the glycosyl acceptor on the equatorial iodide from the axial direction.