- An effective reagent to functionalize alcohols with phosphocholine
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Phosphocholine is a small haptenic molecule that is both a precursor and degradation product of choline. Phosphocholine decorates a number of biologics such as lipids and oligosaccharides. In this study, an air and bench stable phosphocholine donor has been developed and evaluated with a number of alcohol acceptors. Using a one-pot, three-step sequence, (phosphitylation, oxidation, and phosphate deprotection) phosphocholine derivatives are synthesized in high yields. Of particular interest is the synthesis of miltefosine, the lone oral drug approved to treat leishmaniasis. Due to its prohibitive expense ($1500 per g), miltefosine is not accesable for the majority of the world's patients. Based on the described reaction sequence, this drug can be produced for $25 per g.
- Xu, Lianyan L.,Berg, Lawrence J.,Jamin Keith,Townsend, Steven D.
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supporting information
p. 767 - 770
(2020/02/11)
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- D and L etherlipid stereoisomers and liposomes
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A liposome having a lipid bilayer, where the lipid bilayer includes either the L or D stereoisomer of an ether lipid or a non-equal mixture of both. Most preferably the liposome also comprises (a) an underivatized phosphatidylcholine; (b) a sterol; (c) about 5-20 mole % of a phosphatidylethanolamine linked to a dicarboxylic acid at the ethanolamine group of the phosphatidylethanolamine, and (d) greater than about 10 mole % to less than about 30 mole % of either the L or D stereoisomer of an ether lipid. The liposome may be used as an anti-cancer or anti-inflammatory agent.
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Page column 11-12
(2008/06/13)
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- Synthesis of enantiomerically pure ether lipid analogues from D-mannitol
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A new scheme for synthesis of enantiomerically pure ether lipid analogues 3-O-octadecyl-2-O-methyl-sn-glycero-phosphocholine (D-ET-18-OCH3), 1-O-octadecyl-2-O-methyl-sn-glycero-phosphocholine (L-ET-18-OCH3) and their oleyl analogues is described.The key s
- Pinchuk, Anatoly N.,Mitsner, Boris I.,Shvets, Vitaly I.
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- Chiral PAF agonists: Synthesis, theoretical analysis of their stereoelectronic properties and structure activity relationships
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A series of chiral PAF agonists were synthesized. Modifications at the PAF structure were undertaken as far as the C2 substituents and the onium head groups are concerned. In parallel, molecular modelling studies including a MOPAC geometry optimization and the analysis of the electrostatic potential were performed on the newly synthesized and on already known PAF agonists, in order to gain a better insight into the stereoelectronic features required for interaction with the PAF receptor.
- Villa,Pallavicini,Villa,Valoti,Ferri,Maderna
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p. 573 - 613
(2007/10/02)
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- D-mannite derivatives as starting products for the synthesis of phospholipids
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The mannite derivatives have the formula (1) wherein R' and R2, idenal or different, represent when they are identical a straight or branched alkyl, alkenyl or alkynyl group containing from 5 to 24 atoms of carbon which may be substituted by a cycloalkyl residue having from 3 to 6 atoms of carbon, an aryl, benzyloxy, allyloxy, mesyloxy residue and/or halogen atoms and when R' and R2 are different, they represent a straight or branched alkyl group with 1 to 24 atoms or carbon, which may be substituted by a cycloalkyl residue having from 3 to 6 atoms of carbon, an aryl, benzyloxy, allyloxy, mesyloxy residue and/or halogen atoms, with the possibility for R' of being also a trityl group. From said mannite derivatives, it is possible to obtain in a simple way and with good yields the phospholipids in the form of their optical stereo isomers. STR1
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