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Volumn 11, Issue 7, 2000, Pages 1585-1592

Enantioselective synthesis of lyxo-(2R,3R,4R)-C18-phytosphingosine using double stereodifferentiation

Author keywords

[No Author keywords available]

Indexed keywords

SPHINGOLIPID; SPHINGOSINE DERIVATIVE;

EID: 0342749263     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00106-3     Document Type: Article
Times cited : (29)

References (54)
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    • This work is part of the PhD thesis of C. Martin, Orsay, December
    • This work is part of the PhD thesis of C. Martin, Orsay, December 1998.
    • (1998)
  • 2
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    • Reviews: (a) Vance, D. E.; Vance, J. E., Eds.; Elsevier Science: Amsterdam Chapter 12
    • Reviews: (a) Merrill Jr., A. H.; Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins and Membranes; Vance, D. E.; Vance, J. E., Eds.; Elsevier Science: Amsterdam, 1996; Chapter 12, pp. 309-339; (b) Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075-1091; (c) Kolter, T.; Sandhoff, K. Angew. Chem., Int. Ed. 1999, 38, 1532-1568.
    • (1996) In Biochemistry of Lipids, Lipoproteins and Membranes , pp. 309-339
    • Merrill, A.H.1    Sweeley, C.C.2
  • 3
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    • (b)
    • Reviews: (a) Merrill Jr., A. H.; Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins and Membranes; Vance, D. E.; Vance, J. E., Eds.; Elsevier Science: Amsterdam, 1996; Chapter 12, pp. 309-339; (b) Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075-1091; (c) Kolter, T.; Sandhoff, K. Angew. Chem., Int. Ed. 1999, 38, 1532-1568.
    • (1998) Synthesis , pp. 1075-1091
    • Koskinen, P.M.1    Koskinen, A.M.P.2
  • 4
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    • (c)
    • Reviews: (a) Merrill Jr., A. H.; Sweeley, C. C. In Biochemistry of Lipids, Lipoproteins and Membranes; Vance, D. E.; Vance, J. E., Eds.; Elsevier Science: Amsterdam, 1996; Chapter 12, pp. 309-339; (b) Koskinen, P. M.; Koskinen, A. M. P. Synthesis 1998, 1075-1091; (c) Kolter, T.; Sandhoff, K. Angew. Chem., Int. Ed. 1999, 38, 1532-1568.
    • (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 1532-1568
    • Kolter, T.1    Sandhoff, K.2
  • 5
    • 84991428601 scopus 로고    scopus 로고
    • For D-erythro-sphingosine synthesis, see: (a) Ref. 2b;
    • For D-erythro-sphingosine synthesis, see: (a) Ref. 2b; (b) Nugent, T. C.; Hudlicky, T. J. Org. Chem. 1998, 63, 510-520; (c) Hoffman, R. V.; Tao, J. Tetrahedron Lett. 1998, 39, 3953-3956; (d) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985; (e) Khiar, N.; Singh, K.; Garcia, M.; Martin-Lomas, M. Tetrahedron Lett. 1999, 40, 5779-5782; (f) Hertweck, C.; Boland, W. J. Org. Chem. 1999, 64, 4426-4430 and references cited therein.
  • 6
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    • (b)
    • For D-erythro-sphingosine synthesis, see: (a) Ref. 2b; (b) Nugent, T. C.; Hudlicky, T. J. Org. Chem. 1998, 63, 510-520; (c) Hoffman, R. V.; Tao, J. Tetrahedron Lett. 1998, 39, 3953-3956; (d) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985; (e) Khiar, N.; Singh, K.; Garcia, M.; Martin-Lomas, M. Tetrahedron Lett. 1999, 40, 5779-5782; (f) Hertweck, C.; Boland, W. J. Org. Chem. 1999, 64, 4426-4430 and references cited therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 510-520
    • Nugent, T.C.1    Hudlicky, T.2
  • 7
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    • (c)
    • For D-erythro-sphingosine synthesis, see: (a) Ref. 2b; (b) Nugent, T. C.; Hudlicky, T. J. Org. Chem. 1998, 63, 510-520; (c) Hoffman, R. V.; Tao, J. Tetrahedron Lett. 1998, 39, 3953-3956; (d) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985; (e) Khiar, N.; Singh, K.; Garcia, M.; Martin-Lomas, M. Tetrahedron Lett. 1999, 40, 5779-5782; (f) Hertweck, C.; Boland, W. J. Org. Chem. 1999, 64, 4426-4430 and references cited therein.
    • (1998) Tetrahedron Lett. , vol.39 , pp. 3953-3956
    • Hoffman, R.V.1    Tao, J.2
  • 8
    • 0000174699 scopus 로고    scopus 로고
    • (d)
    • For D-erythro-sphingosine synthesis, see: (a) Ref. 2b; (b) Nugent, T. C.; Hudlicky, T. J. Org. Chem. 1998, 63, 510-520; (c) Hoffman, R. V.; Tao, J. Tetrahedron Lett. 1998, 39, 3953-3956; (d) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985; (e) Khiar, N.; Singh, K.; Garcia, M.; Martin-Lomas, M. Tetrahedron Lett. 1999, 40, 5779-5782; (f) Hertweck, C.; Boland, W. J. Org. Chem. 1999, 64, 4426-4430 and references cited therein.
    • (1998) J. Org. Chem. , vol.63 , pp. 3979-3985
    • Hoffman, R.V.1    Tao, J.2
  • 9
    • 0033618299 scopus 로고    scopus 로고
    • (e)
    • For D-erythro-sphingosine synthesis, see: (a) Ref. 2b; (b) Nugent, T. C.; Hudlicky, T. J. Org. Chem. 1998, 63, 510-520; (c) Hoffman, R. V.; Tao, J. Tetrahedron Lett. 1998, 39, 3953-3956; (d) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985; (e) Khiar, N.; Singh, K.; Garcia, M.; Martin-Lomas, M. Tetrahedron Lett. 1999, 40, 5779-5782; (f) Hertweck, C.; Boland, W. J. Org. Chem. 1999, 64, 4426-4430 and references cited therein.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 5779-5782
    • Khiar, N.1    Singh, K.2    Garcia, M.3    Martin-Lomas, M.4
  • 10
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    • (f) and references cited therein
    • For D-erythro-sphingosine synthesis, see: (a) Ref. 2b; (b) Nugent, T. C.; Hudlicky, T. J. Org. Chem. 1998, 63, 510-520; (c) Hoffman, R. V.; Tao, J. Tetrahedron Lett. 1998, 39, 3953-3956; (d) Hoffman, R. V.; Tao, J. J. Org. Chem. 1998, 63, 3979-3985; (e) Khiar, N.; Singh, K.; Garcia, M.; Martin-Lomas, M. Tetrahedron Lett. 1999, 40, 5779-5782; (f) Hertweck, C.; Boland, W. J. Org. Chem. 1999, 64, 4426-4430 and references cited therein.
    • (1999) J. Org. Chem. , vol.64 , pp. 4426-4430
    • Hertweck, C.1    Boland, W.2
  • 11
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    • and references cited therein
    • Murakami, T.; Taguchi, K. Tetrahedron 1999, 55, 989-1004 and references cited therein.
    • (1999) Tetrahedron , vol.55 , pp. 989-1004
    • Murakami, T.1    Taguchi, K.2
  • 40
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    • (a) See Ref. 6(f), (h), (o)
    • (a) See Ref. 6(f), (h), (o);
  • 45
    • 84991422814 scopus 로고    scopus 로고
    • As this work was in progress, a similar dihydroxylation of (Z)-allylic amides leading to ribo- and arabino-phytosphingosins has been reported, see Ref. 6(s). Our method giving access to the lyxo- or the xylo-diastereomers appears to be complementary with the one described in this reference
    • As this work was in progress, a similar dihydroxylation of (Z)-allylic amides leading to ribo- and arabino-phytosphingosins has been reported, see Ref. 6(s). Our method giving access to the lyxo- or the xylo-diastereomers appears to be complementary with the one described in this reference.
  • 51
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    • Cha, J. K.; Christ, N. J.; Kishi, Y. Tetrahedron 1984, 40, 2247-2255. See also: Vedejs, E.; Mc Clure, C. K. J. Am. Chem. Soc. 1986, 108, 1094-1096.
    • (1984) Tetrahedron , vol.40 , pp. 2247-2255
    • Cha, J.K.1    Christ, N.J.2    Kishi, Y.3
  • 52
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    • See also
    • Cha, J. K.; Christ, N. J.; Kishi, Y. Tetrahedron 1984, 40, 2247-2255. See also: Vedejs, E.; Mc Clure, C. K. J. Am. Chem. Soc. 1986, 108, 1094-1096.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 1094-1096
    • Vedejs, E.1    McClure, C.K.2
  • 53
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    • 16 analogue, Ref. 6(h)
    • 16 analogue, Ref. 6(h).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.