Department of Chemistry, GITAM Deemed to be University, Hyderabad, Telangana, India.
Research & Development, Sapala Organics Private Ltd., IDA Mallapur, Hyderabad, Telangana, India.
Nucleosides Nucleotides Nucleic Acids. 2023;42(10):797-806. doi: 10.1080/15257770.2023.2197014. Epub 2023 Apr 11.
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.
使用对甲苯磺酸浸渍的 MCM-41（PTSA-MCM-41）催化剂，在室温下，在乙腈和水（9:1，v/v）中，可在 4-5 小时内以良好至优异的收率实现 5,6-O-亚异丙基相对于 1,2-O-亚异丙基的区域/选择性水解，得到相应的二醇。其他敏感的羟基保护基，如萘基、甲苯酰基、特戊酰基、苯甲酰基和苄基，与该方法兼容。PTSA-MCM-41 催化剂成本低，产物易于从反应混合物中分离，这是该方法的显著优势，使其在多克规模操作中具有实用性。
