30563-15-6

Upstream product

• 19670-51-0 (R)-2,3-dihydroxypropyl n-hexadecanoate 
• 76-83-5 trityl chloride 
• 13383-07-8 (S)-2-O-benzyl-3-O-tritylglycerol aldehyde 
• 112-67-4 n-hexadecanoyl chloride 
• 57416-03-2 (R)-2,2-dimethyl-1,3-dioxolan-4-ylmethyl n-hexadecanoate 
• 57-10-3 1-hexadecylcarboxylic acid 
• 129940-50-7 (S)-tritylglycidol 

Downstream Products

• 19670-51-0 (R)-2,3-dihydroxypropyl n-hexadecanoate 
• 1656-83-3 (R)-1-hydroxy-3-(palmitoyloxy)propan-2-yl oleate 
• 30563-16-7 2,3-dipalmitoyl-1-triphenylmethyl-sn-glycerol 

Relevant academic research and scientific papers

Asymmetric induction during carbonylation of an optically active organopalladium. A novel and versatile route to enantiomeric glycerides.

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.

Synthetic phospholipids as specific substrates for plasma endothelial lipase

We designed and prepared synthetic phospholipids that generate lyso-phosphatidylcholine products with a unique mass for convenient detection by LC–MS in complex biological matrices. We demonstrated that compound 4, formulated either as a Triton X-100 emulsion or incorporated in synthetic HDL particles can serve as a substrate for plasma EL with useful specificity.

Nucleoside conjugates. 10. Synthesis and antitumor activity of 1-β-D-arabinofuranosylcytosine 5'-diphosphate-1,2-dipalmitins

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.