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Volumn 44, Issue 28, 2003, Pages 5221-5223

Efficient one-step synthesis of 2-hydroxy and 2-aminoglycals from selenoglycosides

Author keywords

Carbohydrates; Elimination; Glycals; Oxidation; Selenoglycosides; Selenoxides

Indexed keywords

GLYCAN DERIVATIVE; GLYCOSIDE; SELENIUM DERIVATIVE;

EID: 0038345978     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01216-4     Document Type: Article
Times cited : (14)

References (24)
  • 3
    • 85031175933 scopus 로고    scopus 로고
    • For some recent references, see: (a) Swamy, N. R.; Venkateswarlu, Y. Synthesis 2002, 598-600; (b) Takhi, M.; Abdel-Rahman, A. A.-H.; Schmidt, R. R. Synlett 2001, 427-429; (c) Masson, C.; Soto, J.; Bessodes, M. Synlett 2000, 1281-1282
    • For some recent references, see: (a) Swamy, N. R.; Venkateswarlu, Y. Synthesis 2002, 598-600; (b) Takhi, M.; Abdel-Rahman, A. A.-H.; Schmidt, R. R. Synlett 2001, 427-429; (c) Masson, C.; Soto, J.; Bessodes, M. Synlett 2000, 1281-1282.
  • 4
    • 85031176173 scopus 로고    scopus 로고
    • For examples, see: (a) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon Press: Oxford, 1995; (b) Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082-2089; (c) Ichikawa, Y.; Isobe, M.; Konobe, M.; Goto, T. Carbohydr. Res. 1987, 171, 193-199; (d) Hannessian, S. Total Synthesis of Natural Products: The 'Chiron' Approach; Pergamon Press: Oxford, 1993
    • For examples, see: (a) Levy, D. E.; Tang, C. The Chemistry of C-Glycosides; Pergamon Press: Oxford, 1995; (b) Danishefsky, S. J.; DeNinno, S.; Lartey, P. J. Am. Chem. Soc. 1987, 109, 2082-2089; (c) Ichikawa, Y.; Isobe, M.; Konobe, M.; Goto, T. Carbohydr. Res. 1987, 171, 193-199; (d) Hannessian, S. Total Synthesis of Natural Products: The 'Chiron' Approach; Pergamon Press: Oxford, 1993.
  • 11
    • 0035829356 scopus 로고    scopus 로고
    • For a synthetic route to furanoid glycals via selenoxide elimination, see:
    • For a synthetic route to furanoid glycals via selenoxide elimination, see: Bravo F., Kassou M., Díaz Y., Castillón S. Carbohydr. Res. 336:2001;83-97.
    • (2001) Carbohydr. Res. , vol.336 , pp. 83-97
    • Bravo, F.1    Kassou, M.2    Díaz, Y.3    Castillón, S.4
  • 12
    • 0037193164 scopus 로고    scopus 로고
    • For a recent paper on the use of thioglycosides for the synthesis of 2-hydroxy and 2-amino glycals that was published during the course of this work, see:
    • For a recent paper on the use of thioglycosides for the synthesis of 2-hydroxy and 2-amino glycals that was published during the course of this work, see: Liu J., Huang C.-H., Wong C.-H. Tetrahedron Lett. 43:2002;3447-3448.
    • (2002) Tetrahedron Lett. , vol.43 , pp. 3447-3448
    • Liu, J.1    Huang, C.-H.2    Wong, C.-H.3
  • 18
    • 85031162005 scopus 로고    scopus 로고
    • Required to prevent side reactions caused by selenenic acids and their disproportionation products.
    • Required to prevent side reactions caused by selenenic acids and their disproportionation products.
  • 20
    • 85031168546 scopus 로고    scopus 로고
    • 19 all possess spectroscopic data consistent with those found in the literature
    • 19 all possess spectroscopic data consistent with those found in the literature.
  • 21
    • 85031169587 scopus 로고    scopus 로고
    • 3a-f, 1 equiv.) and N,N-diisopropylethylamine (1.7 equiv.) were dissolved in anhydrous dichloromethane and the solution cooled to 0°C. tert-Butyl hydroperoxide (5.5 M solution in decane, 2.3 equiv.) was added drop-wise over a period of 5 min, and then titanium(IV) isopropoxide (1.0 equiv.) was added. The reaction mixture was stirred under an atmosphere of argon for 2 h, after which time TLC (petrol:ethyl acetate, 4:1) indicated complete consumption of starting material. The yellow solution was concentrated in vacuo, and purified by flash column chromatography
    • Typical experimental procedure: The selenoglycoside ( 3a-f, 1 equiv.) and N,N-diisopropylethylamine (1.7 equiv.) were dissolved in anhydrous dichloromethane and the solution cooled to 0°C. tert-Butyl hydroperoxide (5.5 M solution in decane, 2.3 equiv.) was added drop-wise over a period of 5 min, and then titanium(IV) isopropoxide (1.0 equiv.) was added. The reaction mixture was stirred under an atmosphere of argon for 2 h, after which time TLC (petrol:ethyl acetate, 4:1) indicated complete consumption of starting material. The yellow solution was concentrated in vacuo, and purified by flash column chromatography.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.