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Stereoselective synthesis of 2′-modified nucleosides by using ortho-alkynyl benzoate as a gold(i)-catalyzed removable neighboring participation group†
RSC Advances ( IF 3.9 ) Pub Date : 2017-01-12 00:00:00 , DOI: 10.1039/c6ra27790j Haixin Ding 1, 2, 3, 4, 5 , Chuang Li 3, 4, 5, 6 , Yirong Zhou 3, 4, 5, 6 , Sanguo Hong 1, 2, 3, 4 , Ning Zhang 1, 2, 3, 4 , Qiang Xiao 3, 4, 5, 6
RSC Advances ( IF 3.9 ) Pub Date : 2017-01-12 00:00:00 , DOI: 10.1039/c6ra27790j Haixin Ding 1, 2, 3, 4, 5 , Chuang Li 3, 4, 5, 6 , Yirong Zhou 3, 4, 5, 6 , Sanguo Hong 1, 2, 3, 4 , Ning Zhang 1, 2, 3, 4 , Qiang Xiao 3, 4, 5, 6
Affiliation
In the present paper, we report a novel strategy for highly efficient stereoselective synthesis of 2′-modified nucleosides by using ortho-alkynyl benzoate as neighboring participation group. Subsequently, ortho-alkynyl benzoate can be removed smoothly in the presence of 5 mol% Ph3PAuCl–AgOTf in dichloromethane with H2O (1 eq.) and ethanol (6 eq.) to afford 2′-OH nucleosides in high yields and selectivity.
中文翻译:
通过使用邻炔基苯甲酸酯作为金(i)催化的可移动相邻参与基团的立体选择性合成2'-修饰的核苷†
在本文中,我们报告了一种新的策略,该方法通过使用邻炔基苯甲酸酯作为邻域参与基团来高效立体选择性合成2'-修饰的核苷。随后,可以在含有5 mol%Ph 3 PAuCl-AgOTf的二氯甲烷中,以H 2 O(1当量)和乙醇(6当量)存在下,平稳地除去邻炔基苯甲酸,以高收率得到2'-OH核苷和选择性。
更新日期:2017-01-12
中文翻译:
通过使用邻炔基苯甲酸酯作为金(i)催化的可移动相邻参与基团的立体选择性合成2'-修饰的核苷†
在本文中,我们报告了一种新的策略,该方法通过使用邻炔基苯甲酸酯作为邻域参与基团来高效立体选择性合成2'-修饰的核苷。随后,可以在含有5 mol%Ph 3 PAuCl-AgOTf的二氯甲烷中,以H 2 O(1当量)和乙醇(6当量)存在下,平稳地除去邻炔基苯甲酸,以高收率得到2'-OH核苷和选择性。