119879-76-4Relevant academic research and scientific papers
Synthesis of Chiral Diether and Tetraether Phospholipids: Regiospecific Ring Opening of Epoxy Alcohol Intermediates Derived from Asymmetric Epoxidation
Thompson, David H.,Svendsen, Chris B.,Meglio, Ciro Di,Anderson, Valerie C.
, p. 2945 - 2955 (2007/10/02)
Diether and tetraether phospholipids have been synthesized using chiral epoxy alcohol starting materials (e.g. glycidol 3-nitrobenzenesulfonate esters or tert-butyldiphenylsilyl ethers).These chiral precursors provide control over the stereochemistry, sub
Sulfated glyceroglucolipids as inhibitors of bacterial adherence
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, (2008/06/13)
The subject invention involves pharmaceutical compositions comprising a sulfated glyceroglucolipid having the structure: STR1 wherein n is an integer of from 1 to about 5, R is hydrogen or C1 -C24 acyl or alkyl, R' is hydrogen or C1 -C24 acyl or alkyl, and M+ is a cationic moiety, and methods of treating or preventing gastroduodenal diseases or disorders caused by or associated with H. pylori by administering such compounds.
Regiospecific Opening of Glycidyl Derivatives Mediated by Boron Trifluoride. Asymmetric Synthesis of Ether-Linked Phospholipids
Guivisdalsky, Pedro N.,Bittman, Robert
, p. 4637 - 4642 (2007/10/02)
A short, chiral synthesis of unnatural, cytotoxic ether-linked phospholipids is reported in which the key step is the very high regio- and stereospecific nucleophilic opening of the p-toluenesulfonate (1a, 1b) or tert-butyldiphenylsilyl ether (6a, 6b) derivatives of (R)- or (S)-glycidol with 1-hexadecanol using boron trifluoride etherate as catalyst.The enantiomeric excess of the ring-opened products was >94percent, as judged by 1H NMR and chiral HPLC analysis of the Mosher ester derivatives, indicating that ring opening of 1 and 6 proceeds without significant loss of optical purity.The synthetic strategy of using optically active glycidyl derivatives as the precursor of the glycerol backbone permits the desired enantiomers of 1(3)-O-2-O-methylphosphocholines (5a, 5b) to be generated in good yield and high optical purity from the ring-opened intermediates (2, 7) in three steps without the use of protecting groups.
