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Volumn 7, Issue 3, 1996, Pages 779-786

An efficient stereoselective synthesis of the amino sugar component (E ring) of calicheamicin γ11

Author keywords

[No Author keywords available]

Indexed keywords

CALICHEAMICIN GAMMA1; CARBOHYDRATE DERIVATIVE;

EID: 0029932272     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00074-2     Document Type: Article
Times cited : (17)

References (31)
  • 15
    • 85029984127 scopus 로고    scopus 로고
    • note
    • 7 was the main reaction product. The manuscript relative to this study is presently under preparation.
  • 16
    • 85029998095 scopus 로고    scopus 로고
    • note
    • 8
  • 20
    • 37049171003 scopus 로고
    • a) Methyl β-glycoside 3 and its a anomer 15 (not shown) were prepared from commercially available 2-deoxy-D-ribose by a slight modification (see Experimental) of a previously described procedure: Deriaz, R.E.; Overend, W.G.; Stacey, M.; Wiggins, L.F. J.Chem.Soc. 1949, 2836-2841.
    • (1949) J.Chem.Soc. , pp. 2836-2841
    • Deriaz, R.E.1    Overend, W.G.2    Stacey, M.3    Wiggins, L.F.4
  • 24
    • 85030000615 scopus 로고    scopus 로고
    • note
    • 6,7 of 13 in the complex mixture fraction from 12. However, if present, the regiosomeric C-4 product of 13 is present to an extent not superior to 5%.
  • 25
    • 85029997758 scopus 로고    scopus 로고
    • note
    • a axial).
  • 27
    • 85029997172 scopus 로고    scopus 로고
    • note
    • 8,14
  • 28
    • 85029987355 scopus 로고    scopus 로고
    • note
    • A preliminary attempt to prepare the amino sugar 2 directly by acid methanolysis (at 60°C) of the N-ethyl derivative of aziridine 11 (aziridine 16), was unsuccessful: the desired amino sugar 2 was formula presented obtained only in an unsatisfactory yield (55%) and in a mixture with another glycosidic product (45%) which, at that moment, was not further investigated (see Experimental).
  • 29
    • 85029983443 scopus 로고    scopus 로고
    • note
    • For the bicyclo-type nomenclature used in the case of aziridines 11 and 12, the numbering scheme is the following: formula presented


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.