p-Toluenesulfonic acid adorned on MCM-41: an efficient and mild catalyst for the regio/chemo-selective hydrolysis of terminal isopropylidene acetals.

Rajendra Prasad Samudrala, Srishylam Penjarla, Santhosh Penta, Rambabu Gundla, B Purna Chandra Rao

Nucleosides, nucleotides & nucleic acids 2023

filter terms:

Regio/chemo-selective hydrolysis of a 5,6-O-isopropylidene group over a 1,2-O-isopropylidene group is accomplished to obtain corresponding diols in good to excellent yields within 4-5 hours using the p-toluenesulfonic acid impregnated MCM-41 (PTSA-MCM-41) catalyst in acetonitrile and water (9:1, v/v) at room temperature. Other sensitive hydroxyl protecting groups such as naphthyl, toluoyl, pivaloyl, benzoyl, and benzyl are compatible with this methodology. The low cost of the PTSA-MCM-41 catalyst and ease of separation of product from the reaction mixture are significant advantages of this method, which makes it useful in the multigram scale operation.

Citation

Rajendra Prasad Samudrala, Srishylam Penjarla, Santhosh Penta, Rambabu Gundla, B Purna Chandra Rao. p-Toluenesulfonic acid adorned on MCM-41: an efficient and mild catalyst for the regio/chemo-selective hydrolysis of terminal isopropylidene acetals. Nucleosides, nucleotides & nucleic acids. 2023;42(10):797-806