Literature DB >> 16650394

Inter- and intramolecular glycosylation of exo-glycals promoted by metallic Lewis acids.

Sheng-Jie Hsu1, Hui-Chang Lin, Chun-Hung Lin.   

Abstract

exo-Glycosyl carbonates were employed for inter- and intramolecular glycosylation reactions. A number of metallic Lewis Acids and solvents were examined to enhance the reactivity. The optimum conditions were found to be the use of AlCl3 in 1-nitropropane. The method was demonstrated to be useful for the intermolecular glycosyl transfer of several nucleophiles, including simple alcohols, sugars, and amino acid derivatives; however, intramolecular glycosylations were not successful.

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Year:  2006        PMID: 16650394     DOI: 10.1016/j.carres.2006.04.003

Source DB:  PubMed          Journal:  Carbohydr Res        ISSN: 0008-6215            Impact factor:   2.104


  1 in total

1.  Solvent effects in the nucleophilic substitutions of tetrahydropyran acetals promoted by trimethylsilyl trifluoromethanesulfonate: trichloroethylene as solvent for stereoselective C- and O-glycosylations.

Authors:  Joanna C Kendale; Elizabeth M Valentín; K A Woerpel
Journal:  Org Lett       Date:  2014-07-03       Impact factor: 6.005

  1 in total

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