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Synthesis of 2,3-di-O-phytanyl-1-O-(α-D-glucopyranosyl)-sn-glycerol derivatives, analogues of polar lipids isolated from a halophilic bacterial strain

Abstract

2,3-Di-O-phytanyl-1-O-glucopyranosylglycerol and polar derivatives of its 6′-glucose moiety have been synthesized. The target molecule contains the diphytanyl-sn-glycerol moiety which is α-linked to glucose. The key step in its synthesis involves the coupling of phytanyl bromide and isopropylidene threitol. We also demonstrated that the 6′-hydroxyl group of glycolipids can be functionalized without protection of the sugar moiety.

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Correspondence to Tadao Kamikawa.

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Kamikawa, T., Nogawa, K. & Yamagiwa, Y. Synthesis of 2,3-di-O-phytanyl-1-O-(α-D-glucopyranosyl)-sn-glycerol derivatives, analogues of polar lipids isolated from a halophilic bacterial strain. Glycoconjugate J 10, 235–239 (1993). https://doi.org/10.1007/BF00702205

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Keywords

  • sulfoglycolipid
  • phosphonoglycolipid
  • glycerol ether lipids
  • synthesis