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Journal of Zhejiang University SCIENCE A 2013 Vol.14 No.10 P.760-766

10.1631/jzus.A1300238


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


Author(s):  Li-yan Dai, Qiu-long Shi, Jing Zhang, Xiao-zhong Wang, Ying-qi Chen

Affiliation(s):  . Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China

Corresponding email(s):   dailiyan@zju.edu.cn

Key Words:  2-amino-6-chloropurine, Mitsunobu reaction, bis-Boc protection, Penciclovir (PCV)


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Li-yan Dai, Qiu-long Shi, Jing Zhang, Xiao-zhong Wang, Ying-qi Chen. 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[J]. Journal of Zhejiang University Science A, 2013, 14(7): 760-766.

@article{title="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",
author="Li-yan Dai, Qiu-long Shi, Jing Zhang, Xiao-zhong Wang, Ying-qi Chen",
journal="Journal of Zhejiang University Science A",
volume="14",
number="10",
pages="760-766",
year="2013",
publisher="Zhejiang University Press & Springer",
doi="10.1631/jzus.A1300238"
}

%0 Journal Article
%T 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
%A Li-yan Dai
%A Qiu-long Shi
%A Jing Zhang
%A Xiao-zhong Wang
%A Ying-qi Chen
%J Journal of Zhejiang University SCIENCE A
%V 14
%N 10
%P 760-766
%@ 1673-565X
%D 2013
%I Zhejiang University Press & Springer

TY - JOUR
T1 - 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
A1 - Li-yan Dai
A1 - Qiu-long Shi
A1 - Jing Zhang
A1 - Xiao-zhong Wang
A1 - Ying-qi Chen
J0 - Journal of Zhejiang University Science A
VL - 14
IS - 10
SP - 760
EP - 766
%@ 1673-565X
Y1 - 2013
PB - Zhejiang University Press & Springer
ER -


Abstract: 
Solubility of 2-amino-6-chloropurine in Mitsunobu solvents could be significantly improved after its exocyclic amino group is protected via N-tert-butoxycarbonylation. The bis-Boc protected 2-amino-6-chloropurine also shows excellent activity and N9 selectivity in the coupling with various alcohols by a mitsunobu reaction. Then, 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 process. The coupling of 9 with 5 proceeded regioselectively at a N9 position of purine derivative for a good yield under Mitsunobu conditions.

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