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Volumn 68, Issue 2, 2003, Pages 348-354

First asymmetric synthesis of 6-hydroxy-4-sphingenine-containing ceramides. Use of chiral propargylic alcohols to prepare a lipid found in human skin

Author keywords

[No Author keywords available]

Indexed keywords

HUMAN SKIN;

EID: 0037462337     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo026240+     Document Type: Article
Times cited : (50)

References (50)
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    • note
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    • note
    • D +8.9° (c 1.0, MeOH)).
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    • note
    • 1H NMR spectroscopy.
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    • For examples of high anti:syn ratios in the addition of alkynyl-lithium reagents to 26 in the presence of HMPA, see: (a) Herold, P. Helv. Chim. Acta 1988, 71, 354-362. (b) Gruza, H.; Kiciak, K.; Krasinski, A.; Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 2627-2631.
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    • For examples of high anti:syn ratios in the addition of alkynyl-lithium reagents to 26 in the presence of HMPA, see: (a) Herold, P. Helv. Chim. Acta 1988, 71, 354-362. (b) Gruza, H.; Kiciak, K.; Krasinski, A.; Jurczak, J. Tetrahedron: Asymmetry 1997, 8, 2627-2631.
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    • note
    • The 1,3-oxazolidine carbamate system exists as a pair of rotamers, the interconversion of which is enhanced at high temperature; therefore, proton NMR spectra were recorded at 70 °C.
  • 50
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    • note
    • 13C NMR spectra appear as a pair of singlets (denoted in parentheses).


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