Document Type : Original Research Article

Authors

• Ashok Khanal ¹
• Mark McLachlan II ¹
• Anthony Castro ¹
• Karley Alcala ¹
• Natali De La Cerda ¹
• Adamina Arias ¹
• Abby Miller ¹
• Ivanna Montes ¹
• Sina Ashraf ¹
• Lawrence Tran ²

¹ Chemistry and Biochemistry Department, University of the Incarnate Word, 4301 Broadway, San Antonio, Texas 7820, United States

² School of Osteopathic Medicine, University of the Incarnate Word, 7615 Kennedy Hill Dr, San Antonio, TX 78235, United States

Abstract

Glycols and diols, compounds characterized by the presence of two hydroxyl (-OH) groups, play a pivotal role in numerous chemical and industrial processes owing to their distinctive properties, including water solubility, pharmaceutical applications, antifreeze capabilities, and solvent properties. The principal function of a protecting group lies in temporarily concealing a reactive functional group within a molecule, thereby averting undesirable reactions while allowing other reactions to proceed unhindered. Dimethoxytrityl (DMT) stands out as a commonly employed protecting group in organic synthesis, notably in the realms of oligonucleotide and peptide synthesis. Selective DMT protection of the compounds included in the study were achieved through manipulation of temperature and limiting reagent concentration using cannula transfer in the experiments contributing to the study. The primary hindrance of traditional methodologies for synthesis of mono-DMT-protected compounds lies in the incorporation of high-cost purification of the desired products. This article outlines a chromatography-free methodology for synthesizing mono-DMT-protected derivatives of glycols and diols resulting in high yields and   purity employing economically efficient purification methods such as extraction and precipitation. Characterization is achieved through thin-layer chromatography (TLC) and electrospray ionization mass spectrometry (ESI-MS). Additionally, conducted by undergraduate researchers, this methodology boasts affordability, swiftness, and operational simplicity. Given these merits, it stands as a viable option for inclusion in organic chemistry I and II laboratory projects.

Graphical Abstract

Keywords

• Controlled synthesis
• Chromatography free
• Green Synthesis
• Trityl chemistry
• Organic Synthesis

Main Subjects

• Organic Chemistry

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