A Useful Method for Deprotection of the Protective Allyl Group at the Anomeric Oxygen of Carbohydrate Moieties Using Tetrakis(triphenylphosphine)palladium

Kiyoshi NAKAYAMA; Kouichi UOTO; Kunio HIGASHI; Tsunehiko SOGA; Tsuneo KUSAMA

doi:10.1248/cpb.40.1718

Kiyoshi NAKAYAMA, Kouichi UOTO, Kunio HIGASHI, Tsunehiko SOGA, Tsuneo KUSAMA

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Keywords: deprotection, allyl group, tetrakis(triphenylphosphine)palladium, acetic acid, anomeric position, large-scale synthesis, one-pot reaction

JOURNAL FREE ACCESS

1992 Volume 40 Issue 7 Pages 1718-1720

DOI https://doi.org/10.1248/cpb.40.1718

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Abstract

We have developed a simple method for the deprotection of allyl groups used as a protective group for the anomeric oxygen on a sugar moiety by employing tetrakis(triphenylphosphine) palladium in acetic acid. This method is applicable for not only simple but also complex allyl glycosides, such as natural lipid A intermediates and other important lipid A intermediates. Further, this method would be useful for large-scale preparation.

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