Simple and Efficient Method for the Synthesis of Galactofuranosides

  • Gladys C. Completo Institute of Chemistry, University of The Philippines Los Baños, College, Laguna
  • Reymart V. Sangalang Department of Chemistry, De La Salle University, Taft, Manila
  • Beatrice M. I. Pique Department of Physical Sciences and Mathematics, University of the Philippines Manila, Manila
  • Ruel C. Nacario Institute of Chemistry, University of The Philippines Los Baños, College, Laguna Department of Physical Sciences and Mathematics, University of the Philippines Manila, Manila
DOI: https://doi.org/10.26534/kimika.v27i2.38-49
Keywords: carbohydrate, galactofuranose, iodine, cyclization, β-galactofuranosides

Abstract

An efficient and improved one-pot method for the synthesis of galactofuranosides via iodine-promoted cyclization of galactose diethyl dithioacetal in the presence of alcohol, acting both as solvent and nucleophile, is described. The reaction is carried out at room temperature. Alcohols, such as methanol, cyclohexanol and tert-butanol, were used as nucleophiles for the reaction using 2%, 3% and 5% iodine promoter, respectively. A key finding in this study was that the iodine-promoted cyclization of galactose diethyl dithioacetal with alcohol led to selective formation of β-galactofuranoside allowing the efficient preparation of derivatives of this monosaccharide.
Published
2017-02-02
How to Cite
Completo, G. C., Sangalang, R. V., Pique, B. M. I., & Nacario, R. C. (2017). Simple and Efficient Method for the Synthesis of Galactofuranosides. KIMIKA, 27(2), 38-49. https://doi.org/10.26534/kimika.v27i2.38-49
Issue
Vol. 27 No. 2 (2016)
Section
Research Articles

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