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000051092 084__ $$2WoS$$aChemistry, Organic
000051092 1001_ $$0P:(DE-Juel1)VDB7907$$aBode, S. E.$$b0$$uFZJ
000051092 245__ $$aDiastereomer-differentiating hydrolysis of 1,3-diol-acetonides : a simplified procedure for the separation of syn- and anti-1,3-diols
000051092 260__ $$aWashington, DC$$bACS$$c2002
000051092 300__ $$a619 - 621
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000051092 440_0 $$04749$$aOrganic Letters$$v4$$x1523-7060$$y4
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000051092 520__ $$a[reaction: see text] A new method to facilitate the separation of diastereomeric syn- and anti-1,3-diols is described. The method relies on the different hydrolysis rates of the corresponding diastereomeric acetonides. Treatment of a dichloromethane solution of syn- and anti-1,3-diol-acetonide with a catalytic amount of diluted aqueous hydrochloric acid leads to the selective cleavage of the anti diastereomer. The resulting anti-1,3-diol can be easily separated from the unchanged syn-1,3-diol-acetonide.
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000051092 650_2 $$2MeSH$$aCatalysis
000051092 650_2 $$2MeSH$$aDioxanes: chemical synthesis
000051092 650_2 $$2MeSH$$aHydrolysis
000051092 650_2 $$2MeSH$$aIndicators and Reagents
000051092 650_2 $$2MeSH$$aKinetics
000051092 650_2 $$2MeSH$$aStereoisomerism
000051092 650_7 $$00$$2NLM Chemicals$$aDioxanes
000051092 650_7 $$00$$2NLM Chemicals$$aIndicators and Reagents
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000051092 7001_ $$0P:(DE-Juel1)VDB1106$$aMüller, M.$$b1$$uFZJ
000051092 7001_ $$0P:(DE-Juel1)VDB1800$$aWolberg, M.$$b2$$uFZJ
000051092 773__ $$0PERI:(DE-600)1501522-1$$a10.1021/ol017223u$$gVol. 4, p. 619 - 621$$p619 - 621$$q4<619 - 621$$tOrganic letters$$v4$$x1523-7060$$y2002
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