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Volumn 45, Issue 28, 2004, Pages 5355-5358

Enantioselective synthesis of 1-deoxy-D-gulonojirimycin from a phenylglycinol-derived lactam

Author keywords

Azasugars; Chiral bicyclic lactams; Enantioselective synthesis; Phenylglycinol; Polyhydroxypiperidines

Indexed keywords

1 DEOXY DEXTRO GULONOJIRIMYCIN; CARBOHYDRATE DERIVATIVE; LACTAM DERIVATIVE; PHENYLGLYCINOL; UNCLASSIFIED DRUG;

EID: 2942661314     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.05.089     Document Type: Article
Times cited : (15)

References (43)
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    • Nishimura Y. Atta-ur-Rahman Studies in Natural Products Chemistry. Vol. 16:1995;75-121 Elsevier Science, B.V. Amsterdam
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    • Nishimura, Y.1
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    • For a review, see:
    • For a review, see: Asano N. Glycobiology. 13:2003;93R
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  • 20
    • 0029155704 scopus 로고
    • 1-Deoxy-L-gulonojirimycin is a potent and selective inhibitor of L-fucosidases
    • 1-Deoxy-L-gulonojirimycin is a potent and selective inhibitor of L-fucosidases Legler G., Sütz A.E., Immich H. Carbohydr. Res. 272:1995;17
    • (1995) Carbohydr. Res. , vol.272 , pp. 17
    • Legler, G.1    Sütz, A.E.2    Immich, H.3
  • 24
    • 2942690118 scopus 로고    scopus 로고
    • note
    • 11b for the enantiomer
  • 28
    • 2942687945 scopus 로고    scopus 로고
    • note
    • Minor amounts of the C-8a epimer were also formed. For a discussion of the stereochemistry at the angular C-8a position in bicyclic lactams obtained by related cyclocondensation reactions using aldehyde-esters or ketoacids, see Ref. 13
  • 29
    • 2942633731 scopus 로고    scopus 로고
    • Aldehyde-ester 10 was prepared in 50% overall yield from methyl 4-oxobutanoate, by reaction with vinylmagnesium bromide, followed by silylation of the resulting alcohol and ozonolysis of the vinyl group
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    • 2), 79.8 (C), 127.6 (2 CH), 127.7 ( p -C), 128.4 (2 CH), 137.6 ( ipso -C), 154.9 (CO). For spectroscopic data of related enantiopure N -Boc-3-hydroxy-2-(hydroxy-methyl)piperidines, see: Knight D.W., Lewis N., Share A.C., Haigh D. J. Chem. Soc., Perkin Trans. 1. 1998;3673
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 3673
    • Knight, D.W.1    Lewis, N.2    Share, A.C.3    Haigh, D.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.