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Volumn 53, Issue 26, 1997, Pages 8825-8836

Stereoselective synthesis of 2-deoxy-β-glycosides from glycal precursors. 1. Stereochemistry of the reactions of D-glucal derivatives with phenylsulfenyl chloride and phenylselenenyl chloride

Author keywords

[No Author keywords available]

Indexed keywords

BENZENESULFONIC ACID DERIVATIVE; BETA GLUCAN; CHROMOMYCIN; GLUCONATE CALCIUM; GLYCOSIDE; MITHRAMYCIN; OLIVOMYCIN; SELENIUM DERIVATIVE;

EID: 0030792114     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00571-1     Document Type: Article
Times cited : (75)

References (58)
  • 6
    • 0342377304 scopus 로고
    • Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, This article reviews synthetic efforts in this area through 1987
    • Franck, R. W.; Weinreb, S. M. In Studies in Natural Products Chemistry; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1989; pp. 173. This article reviews synthetic efforts in this area through 1987.
    • (1989) Studies in Natural Products Chemistry , pp. 173
    • Franck, R.W.1    Weinreb, S.M.2
  • 7
    • 0343682520 scopus 로고    scopus 로고
    • note
    • Leading references to the work of Weinreb, Franck, Thiem, Binkley, Crich and Toshima, who have made important contributions to the synthesis of the aureolic acid antibiotics, are provided in ref. 2.
  • 12
    • 0342377303 scopus 로고    scopus 로고
    • note
    • +2-DNA complex (see ref. 32).
  • 18
    • 0021925003 scopus 로고
    • and references therein
    • Thiem, J.; Gerken, M. J. Org. Chem. 1985, 50, 954, and references therein.
    • (1985) J. Org. Chem. , vol.50 , pp. 954
    • Thiem, J.1    Gerken, M.2
  • 40
    • 0343682501 scopus 로고    scopus 로고
    • The factors responsible for the range of results obtained with 14 are not obvious at present
    • The factors responsible for the range of results obtained with 14 are not obvious at present.
  • 42
    • 0342812218 scopus 로고    scopus 로고
    • The synthesis of trisaccharide glycal 23 will be described elsewhere (Roush, W. R.; James, R. A., unpublished research)
    • The synthesis of trisaccharide glycal 23 will be described elsewhere (Roush, W. R.; James, R. A., unpublished research).
  • 44
    • 0343246883 scopus 로고    scopus 로고
    • note
    • These studies were guided by the results reported by Perez and Beau (ref. 26), who observed that the best selectivity in the reactions of 6-deoxy glucal derivatives with PhSeCl was obtained with glycals containing unprotected hydroxyl groups at C(4).
  • 51
    • 0343246882 scopus 로고    scopus 로고
    • note
    • The diastereoselectivity of the reactions of 30a,b with PhSCl and PhSeCl was the same, within experimental error, when checked at the stage of the glycosyl chlorides or acetates.
  • 52
    • 0000717204 scopus 로고
    • In addition to the iodoglycosidation reactions of glycals already noted (refs. 47-48), the C(6)-substituent is also known to influence the stereoselectivity of bromination reactions of glycals (Horton, D.; Priebe, W.; Varela, O. J. Org. Chem. 1986, 51 3479).
    • (1986) J. Org. Chem. , vol.51 , pp. 3479
    • Horton, D.1    Priebe, W.2    Varela, O.3
  • 54
    • 0342812215 scopus 로고
    • Ph. D. Thesis, Indiana University
    • Sebesta, D. P. Ph. D. Thesis, Indiana University, 1992.
    • (1992)
    • Sebesta, D.P.1
  • 55
    • 0343682499 scopus 로고    scopus 로고
    • note
    • Details of the synthesis of 19 are provided in the Supplementary Material section of the paper cited in ref. 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.