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, IraqFollow
Adnan Ibrahim Mohammed, Department of Chemistry, College of Science, University of Kerbala, Karbala, IraqFollow
Baker A. Joda, Department of Chemistry, College of Science, University of Kerbala, Karbala, IraqFollow

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.

Keywords

DFT calculation, Galactose, Propargyl ethers, Terminal alkynes

Article Type

Article

How to Cite this Article

Al-Asadi, Halah Husam Abdulkadhim; Mohammed, Adnan Ibrahim; and Joda, Baker A. (2023) "Synthesis and Structural Determination of 6-O-prop-2-ynyl-1,2:3,4-di-O-Isopropylidene-α-D-Galactose," Baghdad Science Journal: Vol. 20: Iss. 1, Article 22.
DOI: https://doi.org/10.21123/bsj.2022.6914