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Volumn 42, Issue 9, 1999, Pages 815-826

Efficient synthesis of deuterium- and tritium-labeled D-erythro-sphingosine

Author keywords

MTPA derivative; NMR; Sphingosine; Tritium labeling

Indexed keywords

DEUTERIUM; SODIUM BOROHYDRIDE; SPHINGOSINES; STEREOSELECTIVITY;

EID: 0032819750     PISSN: 03624803     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1099-1344(199909)42:9<815::AID-JLCR242>3.0.CO;2-2     Document Type: Article
Times cited : (6)

References (29)
  • 12
    • 0000174699 scopus 로고    scopus 로고
    • Deprotection to sphingosine 1d and the corresponding dihydrosphingosine was not carried out for deuterium-labeled species
    • Hoffman R.V. and Tao J. - J. Org. Chem. 63: 3979-3985 (1998). Deprotection to sphingosine 1d and the corresponding dihydrosphingosine was not carried out for deuterium-labeled species.
    • (1998) J. Org. Chem. , vol.63 , pp. 3979-3985
    • Hoffman, R.V.1    Tao, J.2
  • 18
    • 85166705103 scopus 로고    scopus 로고
    • note
    • We required tritium-labeled sphingosine foi measuring the uptake and subsequent metabolism of free sphingosine by cultured cells and for determining whether sphingosine can be converted to N,N-dimethyl derivatives. In experiments to measure the levels of free sphingosine in biological tissues, tritium-labeled sphingosine may also be useful as an added internal standard to monitor losses during processing.
  • 19
    • 85166704336 scopus 로고    scopus 로고
    • note
    • 4 obtained from Aldrich.
  • 20
    • 85166708356 scopus 로고    scopus 로고
    • note
    • Abbreviations: EI, electron impact; FAB, fast atom bombardment; GC, gas chromatography; IR, infrared (spectrum); mp, melting point; MPLC, medium pressure liquid chromatography; MTPA, α-methoxy-α-(trifluoromethyl)phenylacetate; MS, mass spectrometry or mass spectrum; NMR, nuclear magnetic resonance; PCC, pyridinium chlorochromate; TLC, thin-layer chromatography.
  • 24
    • 85166708590 scopus 로고    scopus 로고
    • in press
    • 19F NMR. A full account of methodology for determining the enantiomeric and diastereomeric purity of sphingosine has been described: Li S., Wilson W.K., and Schroepfer G.J., Jr. - J. Lipid Res. 40: in press (1999).
    • (1999) J. Lipid Res. , vol.40
    • Li, S.1    Wilson, W.K.2    Schroepfer G.J., Jr.3
  • 25
    • 85166705444 scopus 로고    scopus 로고
    • note
    • 1H NMR signals corresponding to the threo epimer.
  • 29
    • 85166709577 scopus 로고    scopus 로고
    • note
    • f 0.20 for 1; ether-hexane 5:95). The residual p-toluenesulfonic acid did not adversely affect the subsequent condensation reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.