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Volumn 9, Issue 17, 2007, Pages 3473-3476

A general approach to the synthesis of 1-deoxy-L-iminosugars

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; HETEROCYCLIC COMPOUND; IMINOSUGAR; PIPERIDINE DERIVATIVE;

EID: 34548181593     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7014847     Document Type: Article
Times cited : (43)

References (34)
  • 1
    • 0003532642 scopus 로고    scopus 로고
    • Stütz, A, Ed, Wiley-VCH: Weinheim, Germany
    • (a) Stütz, A., Ed. Iminosugars as Glycosidase Inhibitors; Wiley-VCH: Weinheim, Germany, 1999.
    • (1999) Iminosugars as Glycosidase Inhibitors
  • 8
    • 24644506429 scopus 로고    scopus 로고
    • For comprehensive reviews see: a
    • For comprehensive reviews see: (a) Afarinkia, K.; Bahar, A. Tetrahedron: Asymmetry 2005, 16, 1239-1287.
    • (2005) Tetrahedron: Asymmetry , vol.16 , pp. 1239-1287
    • Afarinkia, K.1    Bahar, A.2
  • 9
    • 20444432200 scopus 로고    scopus 로고
    • Pearson, M. S. M.; Allaimat, M. M.; Fargeas, V.; Lebreton, J. Eur. J. Org. Chem. 2005, 2159-2191. Carbohydrate-based routes to DNJ and congeners:
    • (b) Pearson, M. S. M.; Allaimat, M. M.; Fargeas, V.; Lebreton, J. Eur. J. Org. Chem. 2005, 2159-2191. Carbohydrate-based routes to DNJ and congeners:
  • 12
    • 0036157638 scopus 로고    scopus 로고
    • Spreidz, J. S.; Stütz, A. E.; Wrodnigg, T. M. Carbohydr. Res. 2002, 337, 183-191 and references cited therein. Non-carbohydrate based routes to DNJ and congeners:
    • (e) Spreidz, J. S.; Stütz, A. E.; Wrodnigg, T. M. Carbohydr. Res. 2002, 337, 183-191 and references cited therein. Non-carbohydrate based routes to DNJ and congeners:
  • 24
    • 34548157938 scopus 로고    scopus 로고
    • The solvent-dependent stereoselective effect should be related to the nature of the organolithium intermediate: as already reported (see farther on, a nude and more reactive ionic couple prevails in THF, while a less reactive non-ionized species is formed in Et2O, driving the reaction towards a better stereoselective outcome: (a) Seyferth, D, King, R. B. Annual Surveys of Organometallic Chemistry, 1-3, Elsevier Publishing Co, Amsterdam, 1965-1967
    • 2O, driving the reaction towards a better stereoselective outcome: (a) Seyferth, D.; King, R. B. Annual Surveys of Organometallic Chemistry, Vol. 1-3, Elsevier Publishing Co.: Amsterdam, 1965-1967.
  • 26
    • 0034741042 scopus 로고    scopus 로고
    • In all our experiments the reported syn stereoselection [Liang, X, Andersch, J, Bols, M. J. Chem. Soc, Perkin Trans. 1 2001, 2136-2157] was never observed. Because of the chemical characteristics of compound 5, such discrepancy could be rationalized assuming that in the reaction medium the catalyst does not complex Garner aldehyde, but it can be sequestrated by the negatively-charged heterocyclic system, without induction of stereoselectivity
    • In all our experiments the reported syn stereoselection [Liang, X.; Andersch, J.; Bols, M. J. Chem. Soc., Perkin Trans. 1 2001, 2136-2157] was never observed. Because of the chemical characteristics of compound 5, such discrepancy could be rationalized assuming that in the reaction medium the catalyst does not complex Garner aldehyde, but it can be sequestrated by the negatively-charged heterocyclic system, without induction of stereoselectivity.
  • 27
    • 34548176014 scopus 로고    scopus 로고
    • An alternative numbering reported on the carbon skeleton has been employed to identify carbon atoms that will belong to the carbohydratelike ring see Table 1
    • An alternative numbering reported on the carbon skeleton has been employed to identify carbon atoms that will belong to the carbohydratelike ring (see Table 1).
  • 31
    • 0029084213 scopus 로고    scopus 로고
    • In the 1C4 chair form, a downward orientation is imposed on the N-Boc substituent owing to the nature of the ring nitrogen atom, resulting in a strong repulsive interaction with the nearly coplanar C-6 methylene group. An upward movement of the ring nitrogen relieves such repulsion leading to a 3S1 conformation. For similar results see: (a) Kilonda, A, Compernolle, F, Hoornaert, G. J. J. Org. Chem. 1995, 60, 5820-5824
    • 1 conformation. For similar results see: (a) Kilonda, A.; Compernolle, F.; Hoornaert, G. J. J. Org. Chem. 1995, 60, 5820-5824.
  • 34
    • 34548167497 scopus 로고    scopus 로고
    • 4, and then leads to the epoxide cleavage.
    • 4, and then leads to the epoxide cleavage.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.