Diastereomer-differentiating hydrolysis of 1,3-diol-acetonides: a simplified procedure for the separation of syn- and anti-1,3-diols.
[reaction: see text] A new method to facilitate the separation of diastereomeric syn- and anti-1,3-diols is described. The method relies on the different hydrolysis rates of the corresponding diastereomeric acetonides. Treatment of a dichloromethane solution of syn- and anti-1,3-diol-acetonide with a catalytic amount of diluted aqueous hydrochloric acid leads to the selective cleavage of the anti diastereomer. The resulting anti-1,3-diol can be easily separated from the unchanged syn-1,3-diol-acetonide.
Bode
Silke E
SE
Institut für Biotechnologie 2, Forschungszentrum Jülich GmbH, D-52425 Jülich, Germany.
Müller
Michael
M
Wolberg
Michael
M
D002384:Catalysis; D004146:Dioxanes / Q000138:chemical synthesis*; D006868:Hydrolysis; D007202:Indicators and Reagents; D007700:Kinetics; D013237:Stereoisomerism
D004146:Dioxanes; D007202:Indicators and Reagents