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Volumn , Issue 23, 2008, Pages 3933-3942

Synthesis of pyranoid and furanoid glycals from glycosyl sulfoxides by treatment with organolithium reagents

Author keywords

Furanoid glycals; Glycosyl sulfoxides; Organolithium reagents; Pyranoid glycals; Sulfoxide ligand exchange

Indexed keywords


EID: 53849113695     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200800318     Document Type: Article
Times cited : (26)

References (114)
  • 10
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    • Ed, P. Fügedi, D. E. Levy, CRC Press, Boca Raton, FL
    • a) D. E. Levy, in The Organic Chemistry of Sugars (Ed.: P. Fügedi, D. E. Levy), CRC Press, Boca Raton, FL, 2006, pp. 269-348;
    • (2006) The Organic Chemistry of Sugars , pp. 269-348
    • Levy, D.E.1
  • 16
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    • Selected contributions: a U. Hünger, J. Ohnsmann, H. Kunz, Angew. Chem. Int. Ed. 2004, 43, 1104-1107;
    • Selected contributions: a) U. Hünger, J. Ohnsmann, H. Kunz, Angew. Chem. Int. Ed. 2004, 43, 1104-1107;
  • 22
  • 62
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    • Ph. D. Thesis, Universidad de Alcalá de Henares Madrid
    • a) M. Casillas, Ph. D. Thesis, Universidad de Alcalá de Henares Madrid, 1999;
    • (1999)
    • Casillas, M.1
  • 67
    • 84982497955 scopus 로고    scopus 로고
    • No thorough study directed towards the optimization of the number of equivalents of the organolithium reagent involved in this transformation has been carried out. According to our proposed mechanism, only 1 equiv. of organolithium reagent will be required for the transformation of fully alkylated sulfoxides into glycals, whereas 2,3-isopropylidene-protected sulfoxides will require a second equivalent of organolithium reagent to react with the acetone liberated in the process (see A. Klemer, G. Rodemeyer, Chem. Ber. 1974, 107, 2612-2614, However, we have observed that the use of 3 equiv. of organolithium reagent works reasonably well in all instances. Sulfoxide 16, bearing a free hydroxy group, was treated with 4 equiv. of nBuLi for its transformation into glycal 19 see Experimental Section
    • No thorough study directed towards the optimization of the number of equivalents of the organolithium reagent involved in this transformation has been carried out. According to our proposed mechanism, only 1 equiv. of organolithium reagent will be required for the transformation of fully alkylated sulfoxides into glycals, whereas 2,3-isopropylidene-protected sulfoxides will require a second equivalent of organolithium reagent to react with the acetone liberated in the process (see A. Klemer, G. Rodemeyer, Chem. Ber. 1974, 107, 2612-2614). However, we have observed that the use of 3 equiv. of organolithium reagent works reasonably well in all instances. Sulfoxide 16, bearing a free hydroxy group, was treated with 4 equiv. of nBuLi for its transformation into glycal 19 (see Experimental Section).
  • 68
    • 53849130902 scopus 로고    scopus 로고
    • The TLC of the final reaction mixture showed only one spot corresponding to the final glycal 8, but compound 8 could only be isolated in 59% yield.
    • The TLC of the final reaction mixture showed only one spot corresponding to the final glycal 8, but compound 8 could only be isolated in 59% yield.
  • 71
    • 27144480331 scopus 로고    scopus 로고
    • Furanoid glycals in synthesis: a A. Choudhury, M. E. Pierce, D. Nguyen, L. Storace, L. Confalone, Tetrahedron Lett. 2005, 46, 8099-8102;
    • Furanoid glycals in synthesis: a) A. Choudhury, M. E. Pierce, D. Nguyen, L. Storace, L. Confalone, Tetrahedron Lett. 2005, 46, 8099-8102;
  • 74
    • 0035829356 scopus 로고    scopus 로고
    • Preparation of furanoid glycals: a F. Bravo, M. Kassou, Y. Díaz, S. Castillón, Carbohydr. Res. 2001, 336, 83-97;
    • Preparation of furanoid glycals: a) F. Bravo, M. Kassou, Y. Díaz, S. Castillón, Carbohydr. Res. 2001, 336, 83-97;
  • 81
    • 53849106031 scopus 로고    scopus 로고
    • No furan formation from glycal 23 was observed. We believe that the presence of Et3N 1, in the eluent mixture for the column chromatography plays a key role in this respect
    • 3N (1%) in the eluent mixture for the column chromatography plays a key role in this respect.
  • 93
    • 53849123903 scopus 로고    scopus 로고
    • 3], and m-CPBA oxidation.
    • 3], and m-CPBA oxidation.
  • 94
    • 0033963867 scopus 로고    scopus 로고
    • For a previous mechanistic study on the formation of glycals under strongly basic conditions using deuteration as a probe, see: T. M. Davis, T. L. Lowary, Carbohydr. Res. 2000, 324, 210-217
    • For a previous mechanistic study on the formation of glycals under strongly basic conditions using deuteration as a probe, see: T. M. Davis, T. L. Lowary, Carbohydr. Res. 2000, 324, 210-217.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.