1-O-Acyl-sn-glycero-3-phosphocholine and 1-O-acyl-sn-glycero-3-phosphoric acid have been prepared selectively and with high yields from the corresponding diols, glycerophosphoryl choline and glycerol-3-phosphate. Starting from the diols, the activated tin ketals were prepared in 2-propanol by reaction with dialkyltin oxide. The intermediates were acylated in the same solvent with long-chain fatty acid chlorides, giving the corresponding 1-acyl-lyso-phospholipids in high yield and with complete regioselectivity. The catalytic nature of the tin-mediated acylation and the relevance of the solvent are discussed.
Download full-text PDF |
Source |
|---|---|
| http://dx.doi.org/10.1039/b604636c | DOI Listing |
Publication Analysis
Top Keywords
Similar Publications
Recent Advances in Photoredox-Mediated Radical Conjugate Addition Reactions: An Expanding Toolkit for the Giese Reaction.
Angew Chem Int Ed Engl
September 2021
Department of Chemistry, Duke University, Box 90346, Durham, NC, 27708-0354, USA.
Photomediated Giese reactions are at the forefront of radical chemistry, much like the classical tin-mediated Giese reactions were nearly forty years ago. With the global recognition of organometallic photocatalysts for the mild and tunable generation of carbon-centered radicals, chemists have developed a torrent of strategies to form previously inaccessible radical intermediates that are capable of engaging in intermolecular conjugate addition reactions. This Review summarizes advances in photoredox-mediated Giese reactions since 2013, with a focus on the breadth of methods that provide access to crucial carbon-centered radical intermediates that can engage in radical conjugate addition processes.
View Article and Find Full Text PDFIodinated Polyesters with Enhanced X-ray Contrast Properties for Biomedical Imaging.
Sci Rep
January 2020
Department of Chemistry, Clemson University, 467 Hunter Laboratories, Clemson, SC, 29634, USA.
Synthetic materials exhibiting contrast imaging properties have become vital to the field of biomedical imaging. However, polymeric biomaterials are lacking imaging contrast properties for deep tissue imaging. This report details the synthesis and characterization of a suite of aryl-iodo monomers, which were used to prepare iodinated polyesters using a pre-functionalization approach.
View Article and Find Full Text PDFImproved synthesis and application of conjugation-amenable polyols from d-mannose.
RSC Adv
January 2020
Laboratory of Molecular Science and Technology, Johan Gadolin Process Chemistry Centre, Åbo Akademi University FI-20500 Turku Finland
A series of polyhydroxyl sulfides and triazoles was prepared by reacting allyl and propargyl d-mannose derivatives with selected thiols and azides in thiol-ene and Huisgen click reactions. Conformational analysis by NMR spectroscopy proved that the intrinsic rigidity and linear conformation of the mannose derived polyol backbone is retained in the final click products in solution. Single crystal X-ray structure determination of one of the compounds prepared further verified that the linear conformation of the polyol segment is also retained in the solid state.
View Article and Find Full Text PDFRapid tin-mediated access to a lysophosphatidylethanolamine (LPE) library: Application to positional LC/MS analysis for hepatic LPEs in non-alcoholic steatohepatitis model mice.
Chem Phys Lipids
October 2016
Graduate School of Health Science, Hokkaido University, North 12, West 5, Kita-ku, Sapporo, 060-0812, Japan. Electronic address:
Even though lysophospholipids have attracted much interest in recent years on account of their unique bioactivity, research related to lysophospholipids is usually hampered by problems associated with standard sample preparation and discrimination of regioisomers. Herein, we demonstrate a quick tin-chemistry-based synthetic route to lysophosphatidylethanolamines (LPEs) and its application in the positional analysis of hepatic LPEs in non-alcoholic steatohepatitis (NASH) model mice. We found that the preference of hepatic LPE regioisomer largely depends on the unsaturation of acyl chain in both control and NASH model mice.
View Article and Find Full Text PDFEfficient tin-mediated synthesis of lysophospholipid conjugates of a TLR7/8-active imidazoquinoline.
Tetrahedron Lett
May 2016
GSK Vaccines, 553 Old Corvallis Road, Hamilton, MT 59840, USA.
The chemical synthesis of lysophospholipids often involves multiple synthetic and chromatographic steps due to the incorporation of the fatty acyl group onto the glycerol scaffold early in the synthesis. We report herein a new protocol for the lysophosphatidylation of alcohols and its application to the synthesis of lysophospholipid conjugates of TLR7/8-active imidazoquinoline . This new procedure, which is based on the tin-mediated regioselective acylation of late-stage phosphoglycerol intermediate , overcomes many of the drawbacks of conventional lysophosphatidylation methods and allows introduction of different fatty acyl groups in the penultimate step.
View Article and Find Full Text PDFWant AI Summaries of new PubMed Abstracts delivered to your In-box?
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!