30563-15-6Relevant articles and documents
Asymmetric induction during carbonylation of an optically active organopalladium. A novel and versatile route to enantiomeric glycerides.
Troitskaya,Sokolov
, p. 389 - 393 (1985)
In the course of carbonylation of optically active [η5-C5H5Feη5- CH5H3CH2NMe2PdCl]2 (1) in prochiral diols, the asymmetric induction of a newly developed chiral centre by a chiral plane has been performed. For 2-O-benzyl- glycerol, the extent of asymmetric induction, that means diastereoselectivity, was found to be about 36%. The protection of a free hydroxyl followed by hydrolysis of a ferrocenoyl derivative resulted in enantiomeric 2-O-benzyl-3-O-trityl-sn-glycerol (4) which can serve as a key intermediate in the synthesis of optically active mono-, di- and tri-substituted glycerides. This methodology has been illustrated by the detailed description of the preparation of 1-palmitoyl-sn-glycerol.
Nucleoside conjugates. 10. Synthesis and antitumor activity of 1-β-D-arabinofuranosylcytosine 5'-diphosphate-1,2-dipalmitins
Hong,An,Schliselfeld,Buchheit,Nechaev,Kirisits,West
, p. 1793 - 1798 (2007/10/02)
Three 1-β-D-arabinofuranosylcytosine 5'-diphosphate-1,2-dipalmitins from L-, D- and DL-α-dipalmitoylphosphatidic acids have been synthesized and their antitumor activity against two ara-C2 resistant L1210 lymphoid leukemia sublines in mice were evaluated. These new prodrugs of ara-C include ara-CDP-L-dipalmitin (1), ara-CDP-D-dipalmitin (2), and ara-CDP-DL-dipalmitin (3). The L and DL isomers produced significant increase in life span (>400%) and four to five long-term survivors (>45 days) out of six animals bearing ip implanted partially ara-C resistant L1210 subline [L1210/ara-C (I)], while the D isomer displayed a marginal activity (ILS 100-121%). In contrast, the L isomer was completely ineffective against deoxycytidine kinase deficient ara-C resistant L1210 subline [L1210/ara-C (II)]. However, the results demonstrate that the L and DL isomers of ara-CDP-dipalmitin are promising new prodrugs of ara-C with improved efficacy.