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Volumn 8, Issue 9, 1997, Pages 1475-1486

A new route to aminosugars from sugar nitrones: Synthesis of 6-deoxynojirimycin

Author keywords

[No Author keywords available]

Indexed keywords

AMINOSUGAR; GLYCOSIDASE INHIBITOR;

EID: 0030990459     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00147-X     Document Type: Article
Times cited : (44)

References (64)
  • 14
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    • Wiley, New York, and references therein
    • (a) Grunanger, P.; Vita-Finzi, P. "Isoxazoles" Wiley, New York, 1991, pp. 649-777, and references therein;
    • (1991) Isoxazoles , pp. 649-777
    • Grunanger, P.1    Vita-Finzi, P.2
  • 24
    • 0000214247 scopus 로고
    • Dhavale, D. D.; Gentilucci, L.; Piazza, M. G.; Trombini, C. Liebigs Ann. Chem. 1992, 1289; see also Mancini, F.; Piazza, G.; Trombini, C. J. Org. Chem. 1991, 56, 4246.
    • (1991) J. Org. Chem. , vol.56 , pp. 4246
    • Mancini, F.1    Piazza, G.2    Trombini, C.3
  • 25
    • 0003643883 scopus 로고
    • Waldmann, H. Ed.; VCH: Weinheim, Germany
    • (a) Hammann, P. Org. Synth. Highlights II, Waldmann, H. Ed.; VCH: Weinheim, Germany, 1995, pp. 323-334;
    • (1995) Org. Synth. Highlights II , pp. 323-334
    • Hammann, P.1
  • 38
  • 39
    • 0000989119 scopus 로고
    • The use of THF as solvent has been reported to give somewhat lower diastereoselectivities compared to ether and dichloromethane: see (a) Chang, Z.-Y; Coates, R. M. J. Org. Chem. 1990, 55, 3464;
    • (1990) J. Org. Chem. , vol.55 , pp. 3464
    • Chang, Z.-Y.1    Coates, R.M.2
  • 41
    • 0343970547 scopus 로고    scopus 로고
    • note
    • Our efforts to carry out the reaction at - 10°C and below in diethylether and dichloromethane and below - 30°C in THF failed due to the insolubility of the nitrones.
  • 42
  • 43
    • 0029928097 scopus 로고    scopus 로고
    • Very interesting inversions of diastereoselectivity in 1,3-addition reactions of lithium derivatives to nitrones in the presence of Lewis acids have been recently reported: (a) Merchan, F. L.; Merino, P.; Rojo, I.; Tejero, T.; Dondoni, A. Tetrahedron: Asymmetry 1996, 7, 667;
    • (1996) Tetrahedron: Asymmetry , vol.7 , pp. 667
    • Merchan, F.L.1    Merino, P.2    Rojo, I.3    Tejero, T.4    Dondoni, A.5
  • 61
    • 0343970523 scopus 로고
    • University of Gottingen, Germany
    • (b) Sheldrick, G. M. (1993), University of Gottingen, Germany.
    • (1993)
    • Sheldrick, G.M.1
  • 62
    • 0343534622 scopus 로고    scopus 로고
    • note
    • Atomic coordinates, bond lengths and angles, and thermal parameters have been deposited at the Cambridge Data Centre.
  • 64
    • 0343098719 scopus 로고    scopus 로고
    • note
    • 3 protons in the region 1.35-1.66 ppm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.