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Volumn 74, Issue 4, 2009, Pages 1766-1769

A short and convenient synthesis of 1-deoxymannojirimycin and N-oxy analogues from D-fructose

Author keywords

[No Author keywords available]

Indexed keywords

1 DEOXYMANNONOJIRIMYCIN; 2 (HYDROXYMETHYL)PIPERIDINE 1,3,4,5 TETRAOL; ALPHA GLUCOSIDASE; BETA GLUCOSIDASE; BETA MANNOSIDASE; CISPLATIN; FRUCTOSE; MANNOSE; NATURAL PRODUCT; NITRONE; OLIGOSACCHARIDE; PIPERIDINE DERIVATIVE; TYROSINE TRANSFER RNA LIGASE; TYROSYL 2 AMINO 2 (2,4,5,8 TETRAHYDROXY 7 OXA 2 AZABICYCLO[3.2.1]OCT 3 YL)ACETIC ACID; UNCLASSIFIED DRUG; XYLAN 1,4 BETA XYLOSIDASE;

EID: 64349095821     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802255t     Document Type: Article
Times cited : (42)

References (87)
  • 38
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    • For a recent review on enantiopure cyclic nitrones, see
    • For a recent review on enantiopure cyclic nitrones, see: Revuelta, J.; Cicchi, S.; Goti, A.; Brandi, A. Synthesis 2007, 485.
    • (2007) Synthesis , pp. 485
    • Revuelta, J.1    Cicchi, S.2    Goti, A.3    Brandi, A.4
  • 43
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    • Kaliappan, K. P.; Das, P. Synlett 2008, 841. See also ref 15d.
    • (e) Kaliappan, K. P.; Das, P. Synlett 2008, 841. See also ref 15d.
  • 51
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    • See ref 15b and 15c. (a) Peer, A.; Vasella, A. Helv. Chim. Acta 1999, 82, 1044.
    • See ref 15b and 15c. (a) Peer, A.; Vasella, A. Helv. Chim. Acta 1999, 82, 1044.
  • 60
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    • See also ref 23a
    • See also ref 23a.
  • 64
    • 0027176072 scopus 로고    scopus 로고
    • D-Fructose as been previously used as a starting material for iminosugar syntheses: (a) Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3613.
    • D-Fructose as been previously used as a starting material for iminosugar syntheses: (a) Furneaux, R. H.; Tyler, P. C.; Whitehouse, L. A. Tetrahedron Lett. 1993, 34, 3613.
  • 69
    • 0010014880 scopus 로고    scopus 로고
    • See Supporting Information. (a) Battaro, J. C.; Bedford, C. D.; Dodge, A. Synth. Commun. 1985, 15, 1333.
    • See Supporting Information. (a) Battaro, J. C.; Bedford, C. D.; Dodge, A. Synth. Commun. 1985, 15, 1333.
  • 71
    • 64349091407 scopus 로고    scopus 로고
    • Azeotropic elimination of water proved necessary for complete conversion of the starting material
    • Azeotropic elimination of water proved necessary for complete conversion of the starting material.
  • 72
    • 64349103722 scopus 로고    scopus 로고
    • 1H NMR spectra.
    • 1H NMR spectra.
  • 83
    • 0037424748 scopus 로고    scopus 로고
    • Compound 13 exhibits spectral data differing from that of its C-5 epimer: Sawada, D.; Takahashi, H.; Ikegami, S. Tetrahedron Lett. 2003, 44, 3085.
    • Compound 13 exhibits spectral data differing from that of its C-5 epimer: Sawada, D.; Takahashi, H.; Ikegami, S. Tetrahedron Lett. 2003, 44, 3085.
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    • and references therein. See Supporting Information. For recent work on cyclic nitrones as radical traps, see
    • See Supporting Information. For recent work on cyclic nitrones as radical traps, see: Han, Y.; Tuccio, B.; Lauricella, R.; Rockenbauer, A.; Zweier, J. L.; Villamena, F. A. J. Org. Chem. 2008, 73, 2533, and references therein.
    • (2008) J. Org. Chem , vol.73 , pp. 2533
    • Han, Y.1    Tuccio, B.2    Lauricella, R.3    Rockenbauer, A.4    Zweier, J.L.5    Villamena, F.A.6


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