CiteScore: 5.0     h-index: 22

Document Type : Original Research Article


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


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

Controlled Synthesis of Mono-Dimethoxytrityl Protected Derivatives of Glycols and Diols Utilizing Chromatography-Free Purification


Main Subjects


©2024 The author(s). This article is licensed under a Creative Commons Attribution 4.0 International License, which permits use, sharing, adaptation, distribution and reproduction in any medium or format, as long as you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The images or other third party material in this article are included in the article’s Creative Commons license, unless indicated otherwise in a credit line to the material. If material is not included in the article’s Creative Commons license and your intended use is not permitted by statutory regulation or exceeds the permitted use, you will need to obtain permission directly from the copyright holder. To view a copy of this license, visit:


Sami Publishing Company remains neutral concerning jurisdictional claims in published maps and institutional affiliations.


Sami Publishing Company

[1] E.A. Peterson, B. Dillon, I. Raheem, P. Richardson, D. Richter, R. Schmidt, H.F. Sneddon, Sustainable chromatography (an oxymoron?), Green Chemistry, 2014, 16, 4060-4075. [Crossref], [Google Scholar], [Publisher]
[2] R. McClain, V. Rada, A. Nomland, M. Przybyciel, D. Kohler, R. Schlake, P. Nantermet, C.J. Welch, Greening flash chromatography, ACS Sustainable Chemistry & Engineering, 2016, 4, 4905-4912. [Crossref], [Google Scholar], [Publisher]
[3] E.A. Aboagye, J.D. Chea, K.M. Yenkie, Systems level roadmap for solvent recovery and reuse in industries, Iscience, 2021, 24. [Crossref], [Google Scholar], [Publisher]
[4] H. Hölzel, M. Muth, D. Lungerich, N. Jux, Addressing Environmental Challenges of Porphyrin Mixtures Obtained from Statistical Syntheses, Chemistry‐Methods, 2021, 1, 142-147. [Crossref], [Google Scholar], [Publisher]
[5] O. Gharib, H. Nasr-Isfahani, M. Bakherad, H. Mighani, Synthesis of New Polyurethanes Based on 5,6,7,8–Tetrabromo–2,3–Dihydro 1,4–Phthalazine Dione, Journal of Applied Organometallic Chemistry, 2022, 2, 129-139. [Crossref], [Publisher]
[6] H.M. Khah, O. Soleimani, Properties and applications of polymers: A mini review, Journal of Chemical Reviews, 2023, 5, 204-220. [Crossref], [Publisher]
[7] A. Bozorgian, A review of investigation of the formation kinetics of TBAC-like clathrate dual hydrates, Journal of Chemical Reviews, 2021, 3, 109-120. [Crossref], [Publisher]
[8] E. Göktürk, H. Erdal, Biomedical applications of polyglycolic acid (PGA), Sakarya University Journal of Science, 2017, 21, 1237-1244. [Crossref], [Google Scholar], [Publisher]
[9] J.J. Sundberg, J. Faergemann, A comparison of pentane-1, 5-diol to other diols for use in dermatology, Expert Opinion on Investigational Drugs, 2008, 17, 601-610. [Crossref], [Google Scholar], [Publisher]
[10] Á. Somoza, Protecting groups for RNA synthesis: an increasing need for selective preparative methods, Chemical Society Reviews, 2008, 37, 2668-2675. [Crossref], [Google Scholar], [Publisher]
[11] J. Salon, B. Zhang, Z. Huang, Mild detritylation of nucleic acid hydroxyl groups by warming up, Nucleosides, Nucleotides and Nucleic Acids, 2011, 30, 271-279. [Crossref], [Google Scholar], [Publisher]
[12] K. Nandhini, D. Al Shaer, F. Albericio, B.G. de la Torre, The challenge of peptide nucleic acid synthesis, Chemical Society Reviews, 2023. [Crossref], [Google Scholar], [Publisher]
[13] K. Klabenkova, A. Fokina, D. Stetsenko, Chemistry of peptide-oligonucleotide conjugates: a review, Molecules, 2021, 26, 5420. [Crossref], [Google Scholar], [Publisher]
[14] B.M. Iselin, Synthesis of N-trityl peptides by the Curtius azide method, Archives of Biochemistry and Biophysics, 1958, 78, 532-538. [Crossref], [Google Scholar], [Publisher]
[15] V. Mäde, S. Els-Heindl, A.G. Beck-Sickinger, Automated solid-phase peptide synthesis to obtain therapeutic peptides, Beilstein Journal of Organic Chemistry, 2014, 10, 1197-1212. [Crossref], [Google Scholar], [Publisher]
[16] A.M. Wawro, T. Muraoka, M. Kato, K. Kinbara, Multigram chromatography-free synthesis of octa (ethylene glycol) p-toluenesulfonate, Organic Chemistry Frontiers, 2016, 3, 1524-1534. [Crossref], [Google Scholar], [Publisher]
[17] A. Khanal, S. Fang, Solid phase stepwise synthesis of polyethylene glycols, Chemistry–A European Journal, 2017, 23, 15133-15142. [Crossref], [Google Scholar], [Publisher]
[18] N. Zekri, R.F. Alamdari, An efficient and selective method for the preparation of triphenylmethyl ethers of alcohols and nucleosides, Canadian Journal of Chemistry, 2021, 88, [Crossref], [Google Scholar], [Publisher]
[19] S.A. Chaubey, J.S. Mishra, R. Mishra, Efficient approach for the tritylation of alcohols using recyclable Lewis acid-based ionic liquid (EMIM· AlCl4), ACS Omega, 2018, 3, 9607-9612. [Crossref], [Google Scholar], [Publisher]
[20] A. Khanal, A potential package for organic chemistry remote teaching, Advanced Journal of Chemistry, Section A, 2021, 4, 115-125. [Crossref], [Publisher]