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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Fox GB, Stackebrandt E, Hespell RB, Gibson J, Maniloff J, Dyer TA, Wolfe RS, Balch WE, Luehrsen KR, Chen KN, Woese CR (1980)Science 209:457–63.
Kushwaha SC, Kates M, Juez G, Rodriguez-Valera F, Kushner DJ (1982)Biochim Biophys Acta 711:19–25.
Boeckel CAA, Westerduin P, van Boom JH (1981)Tetrahedron Lett 22:2819–22.
Al-Hakim AH, Haines AH, Morley C (1985)Synthesis: 207–8.
Yamauchi K, Yamada K, Kinoshita M, Kamikawa T (1991)Bull Chem Soc Japan 64:2088–90.
Paulsen H, Schultz M, Klamann J-D, Waller B, Paul M (1985)Liebigs Ann Chem: 2028–48.
Ohashi K, Kosai S, Arizuka M, Watanabe T, Fukunaga M, Monden K, Uchikoda T, Yamagiwa Y, Kamikawa T (1988)Tetrahedron Lett 29:1189–92.
Ohashi K, Kosai S, Arizuka M, Watanabe T, Yamagiwa Y, Kamikawa T (1989)Tetrahedron 45:2557–70.
Turvey JR, Williams TP (1962)J Chem Soc: 2119–22.
Jacquinet J-C, Petitou M, Duchausoy P, Lederman I, Choay J, Torri G, Sinay (1984)Carbohydr Res 130:221–41.
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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
- glycerol ether lipids