Enantioselective syntheses of D- and L-ribo- and arabino-C18- phytosphingosine from (R)-2,3-0-isopropylidene glyceraldehyde
作者： Johann Mulzer , Clemens Brand
DOI: 10.1016/S0040-4020(01)96078-8
关键词:
摘要: Abstract Practical syntheses of homochiral D- and L-ribo- arabino-C18-phytosphingosine 1 2 from (R)-2,3-0-iso-propylidene glyceraldehyde ( 3 ) are described (Scheme 1), the key steps being: (1) Z -selective olefination (→5) (2) selective monobenzoylation diol 6 (→ 7 ); (3) Mitsunobu-type introduction nitrogen →9); (4) osmylation 9 10 / 11 ).
elsevier.com
sci-hub.se 参考文章(22)
Frank H. Stodola, Lynferd J. Wickerham, Formation of Extracellular Sphingolipids by Microorganisms II. STRUCTURAL STUDIES ON TETRAACETYLPHYTOSPHINGOSINE FROM THE YEAST HANSENULA CIFERRII Journal of Biological Chemistry. ,vol. 235, pp. 2584- 2585 ,(1960) , 10.1016/S0021-9258(19)76917-8
Erich Baer, Hermann O.L. Fischer, STUDIES ON ACETONE-GLYCERALDEHYDE: IV. PREPARATION OF d(+)-ACETONE GLYCEROL Journal of Biological Chemistry. ,vol. 128, pp. 463- 473 ,(1939) , 10.1016/S0021-9258(18)73702-2
Oyo Mitsunobu, The Use of Diethyl Azodicarboxylate and Triphenylphosphine in Synthesis and Transformation of Natural Products Synthesis. ,vol. 1981, pp. 1- 28 ,(1981) , 10.1055/S-1981-29317
Wilfried Schwab, Volker Jäger, 4‐Hydroxylierung von Isoxazolinen; Synthese von rac‐Phytosphingosin (ribo‐2‐Amino‐1,3,4‐octadecantriol) Angewandte Chemie. ,vol. 93, pp. 578- 579 ,(1981) , 10.1002/ANGE.19810930611
W. Stoffel, Chemistry and biochemistry of sphingosine bases. Chemistry and Physics of Lipids. ,vol. 11, pp. 318- 334 ,(1973) , 10.1016/0009-3084(73)90068-6
Edwin. Vedejs, Cynthia K. McClure, Hyperconjugative effects of allylic substituents are not important in osmylations Journal of the American Chemical Society. ,vol. 108, pp. 1094- 1096 ,(1986) , 10.1021/JA00265A048
Sunggak Kim, Heung Chang, Wan Ju Kim, Selective benzoylation of diols with 1-(benzoyloxy)benzotriazole Journal of Organic Chemistry. ,vol. 50, pp. 1751- 1752 ,(1985) , 10.1021/JO00210A036
Fritz Reindel, A. Weickmann, S. Picard, Karl Luber, Paul Turula, Über Pilzcerebrin. II Justus Liebig's Annalen der Chemie. ,vol. 544, pp. 116- 137 ,(1940) , 10.1002/JLAC.19405440108
Jill Gigg, Roy Gigg, A synthesis of phytosphingosines from D-galactose Journal of The Chemical Society C: Organic. ,vol. 20, pp. 1876- 1879 ,(1966) , 10.1039/J39660001876
Karl-Anders Karlsson, O. Hassel, Chr. Römming, D. R. Sparrow, Studies on sphingosines. 7. The existence of C18- and C20-phyto-sphingosine in animal tissues. Acta Chemica Scandinavica. ,vol. 18, pp. 2397- 2398 ,(1964) , 10.3891/ACTA.CHEM.SCAND.18-2397