The reaction of thiolates with 2,3-dibromo-1-propanol revisited: application to the synthesis of bis(fattyalkylthio)propanols
| Autor: | Adrian L. Schwan, Michael D Gernon, Robert H. Notter, Joseph G. Turcotte, Min Wu, Jennifer L. Snelgrove, Yvonne Lear |
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| Rok vydání: | 1999 |
| Předmět: |
1h nmr spectroscopy
Magnetic Resonance Spectroscopy Propanols Stereochemistry Organic Chemistry Cell Biology Nuclear magnetic resonance spectroscopy Biochemistry chemistry.chemical_compound 1-Propanol Models Chemical chemistry Yield (chemistry) Alcohol products Sulfhydryl Compounds Propionates Molecular Biology Long chain |
| Zdroj: | Chemistry and Physics of Lipids. 101:215-222 |
| ISSN: | 0009-3084 |
| Popis: | This work compares two reaction schemes for preparing 2,3-bis(fattyalkylthio)-1-propanols for further synthetic adaptation as hydrophobic analogs of lung surfactant phosphatidylcholines. An attempt to prepare 2,3-bis(fattyalkylthio)-1-propanols based on the previously published methods of Bell and co-workers (B.R. Ganong, C.R. Loomis, Y.A. Hannun, R.M. Bell, 1986. Proc. Natl. Acad. Sci. USA 83, 1184-1188; B.R. Ganong, R.M. Bell, 1987. Methods Enzymol. 141, 313-320; J.P. Walsh, L. Fahrner, R.M. Bell, 1990. J. Biol. Chem. 265, 4374-4381) was found to give the rearranged 1,3-bis(fattyalkylthio)-2-propanols as major products. As a reliable alternative, the reaction of ethyl 2,3-dibromopropionate with 2 equivalents of long chain sodium n-alkanethioates gave the corresponding ethyl 2,3-bis(n-alkylthio)propionates, which were then reduced with LiAlH4 to yield the desired 2,3-bis(fattyalkylthio)-1-propanols. Both 13C and 1H NMR spectroscopy were used to differentiate the two possible 1,3- and 2,3-dithio substituted alcohol products and to rigorously assign their structures. |
| Databáze: | OpenAIRE |
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