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Synthesis and Structural Determination of 6-O-prop-2-ynyl-1,2:3,4-di-O-Isopropylidene-α-D-Galactose

Authors

  • Halah Husam Abdulkadhim Al-Asadi Department of Chemistry, College of Science, University of Kerbala, Karbala, Iraq
  • Adnan Ibrahim Mohammed Department of Chemistry, College of Science, University of Kerbala, Karbala, Iraq https://orcid.org/0000-0002-3038-9729
  • Baker A. Joda Department of Chemistry, College of Science, University of Kerbala, Karbala, Iraq https://orcid.org/0000-0003-2758-5582

DOI:

https://doi.org/10.21123/bsj.2022.6914

Keywords:

DFT calculation, Galactose, Propargyl ethers, Terminal alkynes

Abstract

In this work, an important sugar alkynyl ether has been synthesized in two subsequent steps starting from commercially available D-galactose (3). This kind of compounds is highly significant in the synthesis of biologically active molecules such as 1,2,3-triazole and isoxazoles. In the first step, galactose (3) was reacted with acetone in the presence of anhydrous copper (II) sulfate to produce 1,2:3,4-di-O-isopropylidene-α-D-galactose (4) in good yield. The latter was reacted with excess of 3-bromoprop-1-yne in DMF in the presence of NaOH pellets to afford the target molecule 5 in a very good yield. The temperature of this step is crucial in determining the reaction yield. The exact structure of compound 5 is identified using NMR technique and DFT calculations. 

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