Bulletin of the Korean Chemical Society

  • 제30권3호
  • /
  • Pages.695-699
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  • 2009
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  • 0253-2964(pISSN)
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  • 1229-5949(eISSN)
대한화학회 (Korean Chemical Society)
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Stereoselective Transformation of Phytosphingosine to Safingol

  • Kim, Na-Ri (Department of Chemistry, Seoul Women’s University) ;
  • Lee, Sun-Hee (Department of Chemistry, Seoul Women’s University) ;
  • Namgoong, Sung-Keon (Department of Chemistry, Seoul Women’s University)
  • 발행 : 2009.03.20
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초록

A short and efficient synthesis of (2S,3S)-safingol from commercially available D-ribo-(2S,3S,4R)-phytosphingosine is described. The highlights of the synthesis are a stereoselective one-pot transformation of a diol into an epoxide under phase transfer catalytic conditions and a regioselective epoxide-opening reduction with a hydride reagent.

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참고문헌

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피인용 문헌

  1. ChemInform Abstract: Stereoselective Transformation of Phytosphinosine to Safingol. vol.40, pp.32, 2009, https://doi.org/10.1002/chin.200932195
  2. A general and concise asymmetric synthesis of sphingosine, safingol and phytosphingosines via tethered aminohydroxylation vol.8, pp.22, 2010, https://doi.org/10.1039/C0OB00117A
  3. A General Synthesis of Sphinganines through Multicomponent Catalytic Asymmetric Aziridination vol.2014, pp.7, 2014, https://doi.org/10.1002/ejoc.201301766
  4. ‘Chiron’ approach to stereoselective synthesis of sphinganine and unnatural safingol, an antineoplastic and antipsoriatic agent vol.6, pp.18, 2016, https://doi.org/10.1039/C5RA27342K
  5. - and Enantioselective Henry Reactions of Aliphatic Aldehydes and Application to the Synthesis of Safingol vol.19, pp.49, 2013, https://doi.org/10.1002/chem.201303650
  6. Stereoselective synthesis and antiproliferative activity of the isomeric sphinganine analogues vol.472, pp.None, 2019, https://doi.org/10.1016/j.carres.2018.09.008