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Volumn 69, Issue 17, 2004, Pages 5699-5704

Effective, high-yielding, and stereospecific total synthesis of D-erythro-(2R,3S)-sphingosine from D-ribo-(2S,3S,4R)-phytosphingosine

Author keywords

[No Author keywords available]

Indexed keywords

SYNTHESIS (CHEMICAL);

EID: 4043175402     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049277y     Document Type: Article
Times cited : (25)

References (64)
  • 12
    • 0034602328 scopus 로고    scopus 로고
    • Selected publications on recent syntheses of D-erythro-sphingosine (a) He, L. L.; Byun, H. S.; Bittman, R. J. Org. Chem. 2000, 65, 7627-7633.
    • (2000) J. Org. Chem. , vol.65 , pp. 7627-7633
    • He, L.L.1    Byun, H.S.2    Bittman, R.3
  • 22
    • 0002694812 scopus 로고
    • Cevc, G., Ed.; Marcel Dekker: New York
    • For reviews on D-erythro-sphingosine synthesis, see (a) Byun, H. S.; Bittman, R. In Phospholipids Handbook; Cevc, G., Ed.; Marcel Dekker: New York, 1993; pp 97-140.
    • (1993) Phospholipids Handbook , pp. 97-140
    • Byun, H.S.1    Bittman, R.2
  • 24
    • 0011447582 scopus 로고    scopus 로고
    • Gunstone, F. D., Ed.; Sheffield Academic Press: Sheffield, U.K.; CRC Press: Boca Raton, FL
    • (c) Jung, K. H.; Schmidt, R. R. In Lipid Synthesis and Manufacture; Gunstone, F. D., Ed.; Sheffield Academic Press: Sheffield, U.K.; CRC Press: Boca Raton, FL, 1999; pp 208-249.
    • (1999) Lipid Synthesis and Manufacture , pp. 208-249
    • Jung, K.H.1    Schmidt, R.R.2
  • 26
    • 4043133975 scopus 로고    scopus 로고
    • note
    • Phytosphingosine [(2S,3S,4R-2-amino-1,3,4-octadecanetriol] is now readily available from a yeast fermentation process. For information, contact Cosmoferm B. V. Wateringseweg 1, P.O. Box 386, 2600 AJ Delft, The Netherlands, Fax +31(15)2794120; e-mail: info@ coamoferm.com.
  • 37
    • 4043176446 scopus 로고    scopus 로고
    • U.S. patent office 1955, US 2718520
    • Slack, R. U.S. patent office 1955, US 2718520.
    • Slack, R.1
  • 44
    • 4043092934 scopus 로고    scopus 로고
    • note
    • Conversion of phytosphingosine 2 into diol 5 has been performed on multigram scale (226 g starting material 2) without column Chromatographic purification. This seven-step one-pot event was performed with minor adjustments of the here-described method in an overall yield of 58% and high chemical purity. For the detailed experimental protocol, see Supporting Information.
  • 59
    • 0035208523 scopus 로고    scopus 로고
    • Hertweck, C.; Sebek, P.; Svatos, A. Synlett 2001, 1965-1967; Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393-4398.
    • (2001) Synlett , pp. 1965-1967
    • Hertweck, C.1    Sebek, P.2    Svatos, A.3
  • 60
    • 0019817638 scopus 로고
    • Hertweck, C.; Sebek, P.; Svatos, A. Synlett 2001, 1965-1967; Tkaczuk, P.; Thornton, E. R. J. Org. Chem. 1981, 46, 4393-4398.
    • (1981) J. Org. Chem. , vol.46 , pp. 4393-4398
    • Tkaczuk, P.1    Thornton, E.R.2
  • 61
    • 4043071482 scopus 로고    scopus 로고
    • note
    • With slight modifications of the here-described procedure, p-toluenesulfonyl derivative 13 can be transformed into sphingosine 1 on a multigram scale (65 g starting material of 13) via a one-pot six-step methodology in high overall yield (60%), requiring only singly column chromatography purification step. For the detailed experimental protocol see Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.