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Volumn , Issue 10, 1999, Pages 1551-1554

A concise synthesis of a trehazolamine epimer with moderate α- mannosidase inhibitory activity starting from D-mannose

Author keywords

Carbocycles; Carbohydrates; Glycosidases; Radical reactions; Samarium

Indexed keywords

MANNOSE; MANNOSIDASE; TETRAHAZOLAMINE; UNCLASSIFIED DRUG;

EID: 0032826650     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-3168     Document Type: Article
Times cited : (29)

References (49)
  • 3
    • 0032473838 scopus 로고    scopus 로고
    • For recent reviews on applications of samarium diiodide in organic synthesis, see: (a) Molander, G. A.; Harris, G. R. Tetrahedron 1998, 54, 3321.
    • (1998) Tetrahedron , vol.54 , pp. 3321
    • Molander, G.A.1    Harris, G.R.2
  • 8
    • 0000579244 scopus 로고
    • For examples of ketyl radical cyclizations of carbohydrate derivatives promoted by samarium diiodide, see: (a) Enholm, E. J.; Trivellas, A. J. Am. Chem. Soc. 1989, 111, 6463.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 6463
    • Enholm, E.J.1    Trivellas, A.2
  • 38
    • 0345582625 scopus 로고    scopus 로고
    • note
    • Giese and co-workers have recently applied this approach to the preparation of 2 (ref. 4aa).
  • 40
    • 0345150748 scopus 로고    scopus 로고
    • note
    • The preparation of keto-oximes 4 and 5 will be described in full elsewhere.
  • 41
    • 0345150746 scopus 로고    scopus 로고
    • note
    • When our work was in progress (ref. 6), Giese and co-workers published (ref. 4aa) a similar approach for the control of the stereoselectivity of the carbocyclization of a related substrate.
  • 43
    • 0345150745 scopus 로고    scopus 로고
    • note
    • 2O): 4.18 (ddd, 1H, J=1.1 Hz, J=5.7 Hz, J=8.0 Hz, H-2), 3.97 (d, 1H, J=6.4 Hz), 3.94 (s, 2H, H-6, H-6′), 3.74 (d, 1H, J=1.7 Hz), 3.42 (d, 1H, J=8.0 Hz, H-1).
  • 44
    • 0344720473 scopus 로고    scopus 로고
    • note
    • 2/McOH 10 : 1) to give 7 (61 mg, 86%) as a white solid.
  • 48
    • 0345150737 scopus 로고    scopus 로고
    • note
    • 4aa


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.