jo9822028_si_002.pdf (782.97 kB)
Synthetic Approaches to Novel Archaeal Tetraether Glycolipid Analogues†
journal contribution
posted on 1999-04-13, 00:00 authored by Grégory Lecollinet, Rachel Auzély-Velty, Mathieu Danel, Thierry Benvegnu, Grahame Mackenzie, John W. Goodby, Daniel PlusquellecSymmetrical and unsymmetrical archaeal tetraether glycolipid analogues have been prepared. The
syntheses are based upon the elaboration of lipid cores from versatile chiral starting materials
followed by simultaneous or sequential introduction of polar headgroups. Three pathways (A−C)
were elaborated for the synthesis of stereochemically defined lipids 14−16 characterized by a
straight bridging spacer and two dihydrocitronellyl chains attached to glycerol units at the sn-3
and sn-2 positions, respectively. Pathway C appeared to be particularly advantageous for the
synthesis of tetraether 9, which possesses a cyclopentane unit as found in thermoacidophilic lipids.
Diglycosylated lipids 4−6 were produced in 49−53% yields by reaction of diols 14−16 with β-d-galactofuranosyl donor 31, whereas unsymmetrical lipids possessing either two different carbohydrate units 7 or a saccharidic moiety and a phosphate group 8 were efficiently prepared from
monoprotected diol 35. These compounds represent the first examples of tetraether-type analogues
containing a phosphate unit and/or glycosyl moieties.
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sequential introductionunsymmetrical lipidsmonoprotected diol 35phosphate group 8dihydrocitronellyl chainsPathway Ccyclopentane unitunsymmetrical archaeal tetraether glycolipid analoguesSynthetic Approachessaccharidic moietyglycerol unitssynthesislipid corescarbohydrate units 7thermoacidophilic lipidstetraether 9phosphate unitsn
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