Accelerated effect on Mitsunobu reaction via bis-N-tert-butoxycarbonylation protection of 2-amino-6-chloropurine and its application in a novel synthesis of penciclovir

作     者：Li-yan DAI Qiu-long SHI Jing ZHANG Xiao-zhong WANG Ying-qi CHEN 

作者机构：Department of Chemical and Biological Engineering Zhejiang University 

出 版 物：《Journal of Zhejiang University-Science A(Applied Physics & Engineering)》 (浙江大学学报（英文版）A辑（应用物理与工程）)

年 卷 期：2013年第14卷第10期

页      面：760-766页

核心收录：

学科分类：1007[医学-药学(可授医学、理学学位)] 10[医学] 

主　　题：2-amino-6-chloropurine Mitsunobu reaction bis-Boc protection Penciclovir(PCV) 

摘      要：Solubility of 2-amino-6-chloropurine in Mitsunobu solvents could be significantly improved after its exocyclic amino group is protected via *** bis-Boc protected 2-amino-6-chloropurine also shows excellent activity and N9 selectivity in the coupling with various alcohols by a Mitsunobu ***,a new practical and efficient method is established for the synthesis of penciclovir(PCV) from bis-Boc-2-amino-6-chloropurine 9 and the side chain of 5-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxane 5—the latter being a more easily prepared cyclic precursor of the diacetate side chain used in the conventional *** coupling of 9 with 5 proceeded regioselectively at a N9 position of purine derivative for a good yield under Mitsunobu conditions.