Controlled Synthesis of Mono-Dimethoxytrityl Protected Derivatives of Glycols and Diols Utilizing Chromatography-Free Purification
نویسندگان
1 Chemistry and Biochemistry Department, University of the Incarnate Word, 4301 Broadway, San Antonio, Texas 7820, United States
2 Chemistry and Biochemistry Department, University of the Incarnate Word, 4301 Broadway, San Antonio, Texas 7820, United States
3 Chemistry and Biochemistry Department, University of the Incarnate Word, 4301 Broadway, San Antonio, Texas 7820, United States
4 Chemistry and Biochemistry Department, University of the Incarnate Word, 4301 Broadway, San Antonio, Texas 7820, United States
5 School of Osteopathic Medicine, University of the Incarnate Word, 7615 Kennedy Hill Dr, San Antonio, TX 78235, United States
6 Chemistry and Biochemistry Department, University of the Incarnate Word, 4301 Broadway, San Antonio, Texas 7820, United States
7 Chemistry and Biochemistry Department, University of the Incarnate Word, 4301 Broadway, San Antonio, Texas 7820, United States
8 Chemistry and Biochemistry Department, University of the Incarnate Word, 4301 Broadway, San Antonio, Texas 7820, United States
9 Chemistry and Biochemistry Department, University of the Incarnate Word, 4301 Broadway, San Antonio, Texas 7820, United States
10 Chemistry and Biochemistry Department, University of the Incarnate Word, 4301 Broadway, San Antonio, Texas 7820, United States
doi
10.48309/ajca.2024.436668.1479چکیده
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.
