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  • Synthesis and absolute configuration of novel N,O-psiconucleosides using (R)-N-phenylpantolactam as a resolution agent.

Synthesis and absolute configuration of novel N,O-psiconucleosides using (R)-N-phenylpantolactam as a resolution agent.

The Journal of organic chemistry (2008-07-30)
Pelayo Camps, Tània Gómez, Diego Muñoz-Torrero, Jordi Rull, Laura Sánchez, Francesca Boschi, Mauro Comes-Franchini, Alfredo Ricci, Teresa Calvet, Mercè Font-Bardia, Erik De Clercq, Lieve Naesens
ABSTRACT

A series of novel N,O-psiconucleosides has been prepared in both enantiomeric forms by resolution of an advanced racemic synthetic intermediate using (R)-N-phenylpantolactam as a chiral resolution agent. The absolute configuration of all of these compounds has been unequivocally established by chemical correlation with the novel (R)- or (S)-1-methyl-5-phenylpyrrolidine-2,3-dione, prepared from the known (R)- and (S)-1-methyl-5-phenylpyrrolidin-2-one, respectively.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
DL-α-Hydroxy-β,β-dimethyl-γ-butyrolactone, purum, ≥97.0% (T)
Sigma-Aldrich
(S)-(+)-Pantolactone, 97%
Sigma-Aldrich
D-(−)-Pantolactone, 99%