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A Practical Method for Regioselective 5′-O-tert-Butyldimethylsilyl Deprotection of Persilylated Nucleosides by Methanolic Phosphomolybdic Acid
Synlett ( IF 2 ) Pub Date : 2018-10-12 , DOI: 10.1055/s-0037-1610300
Shan-Shan Gong 1 , Qi Sun 1 , Hua-Shan Huang , Rui Kong , Xiu-An Zheng , Wei-Jie Chen , Shuai-Bo Han , De-Yun Zeng
Affiliation  

In nucleoside/nucleotide chemistry, the regioselective cleavage of 5′-O-TBS groups of persilylated nucleosides is a desired approach for structural functionalization at the 5′-position. However, efficient and practical methods for this purpose are still limited. In our research, we found that homogeneous methanolic phosphomolybdic acid (PMA) efficiently catalyzes the regioselective deprotection of 5′-O-TBS groups of a diversity of persilylated nucleoside substrates and can be applied in practical synthesis at scales of up to 15 g. 31P NMR results indicated that an anion cluster forms and the Lewis acidity of homogeneous PMA is organic-solvent dependent. The efficacy and pronounced regioselectivity of methanolic PMA occurs as a result of a lowering of the Lewis acid strength upon solvation of the molybdophosphate anions.

中文翻译:

甲醇磷钼酸区域选择性 5'-O-叔丁基二甲基甲硅烷基脱保护过甲硅烷基化核苷的实用方法

在核苷/核苷酸化学中,全甲硅烷基化核苷的 5'-O-TBS 基团的区域选择性切割是 5' 位结构功能化的理想方法。然而,用于此目的的有效和实用的方法仍然有限。在我们的研究中,我们发现均相甲醇磷钼酸 (PMA) 可有效催化多种全甲硅烷基化核苷底物的 5'-O-TBS 基团的区域选择性脱保护,并可用于实际合成,规模可达 15 g。31P NMR 结果表明形成了阴离子簇,且均相 PMA 的路易斯酸度取决于有机溶剂。甲醇 PMA 的功效和显着的区域选择性是由于磷酸钼阴离子溶剂化后路易斯酸强度降低的结果。
更新日期:2018-10-12
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