Trityl groups are a very common hydroxyl-protecting group in the solid phase and organic synthesis. They can selectively protect less crowded alcohol primarily due to its large size. The Trityl group is inert toward bases, oxidizing agents, reducing agents, and nucleophiles, but it is fragile under acidic conditions. Trityl protection has wide applications, especially in a solid-phase synthesis that includes DNA, RNA, and peptides. Trityl-protected solid support and nucleosides have been used during the coupling step in DNA oligonucleotide synthesis. Similarly, tosylation transforms the stable alcohol group into a fragile leaving group, sulfonic ester/tosylate, and is considered as a hub for organic synthesis.<br/>Glycols and diols were mono-tritylated under controlled and mild conditions. In the first step, complete consumption of trityl chloride was monitored by TLC before the reaction mixture was extracted to remove excess glycols, diols and pyridinium salt. The majority of di-tritylated byproduct and remaining pyridine was removed by precipitation. The mono-tritylated product was subjected to tosylation in presence of sodium hydroxide. Trityl ether tosylate derivatives of glycol and diols were synthesized with a higher overall yield. Products were analyzed with TLC and ESI. The product does not require any high-cost flash column chromatographic separation.

Green synthesis of trityl ether tosylate of glycols and diols

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