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
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...
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| Published in | Journal of Zhejiang University. A. Science Vol. 14; no. 10; pp. 760 - 766 |
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| Main Authors | , , , , |
| Format | Journal Article |
| Language | English |
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Hangzhou
Zhejiang University Press
01.10.2013
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| 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-l,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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| AbstractList | 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. 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-l,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. 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. |
| Author | Li-yan DAI Qiu-long SHI Jing ZHANG Xiao-zhong WANG Ying-qi CHEN |
| AuthorAffiliation | Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China |
| Author_xml | – sequence: 1 givenname: Li-yan surname: Dai fullname: Dai, Li-yan email: dailiyan@zju.edu.cn organization: Department of Chemical and Biological Engineering, Zhejiang University – sequence: 2 givenname: Qiu-long surname: Shi fullname: Shi, Qiu-long organization: Department of Chemical and Biological Engineering, Zhejiang University – sequence: 3 givenname: Jing surname: Zhang fullname: Zhang, Jing organization: Department of Chemical and Biological Engineering, Zhejiang University – sequence: 4 givenname: Xiao-zhong surname: Wang fullname: Wang, Xiao-zhong organization: Department of Chemical and Biological Engineering, Zhejiang University – sequence: 5 givenname: Ying-qi surname: Chen fullname: Chen, Ying-qi organization: Department of Chemical and Biological Engineering, Zhejiang University |
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| Cites_doi | 10.1016/0040-4039(96)00211-0 10.1021/jm00359a023 10.1055/s-1981-29317 10.1021/jo060430t 10.1080/07328318408081287 10.1081/SCC-120027717 10.1021/jo000983i 10.1016/S0040-4020(01)87878-9 10.1128/AAC.22.1.55 10.1128/AAC.38.4.719 10.1016/S0006-291X(82)80109-5 10.1081/SCC-120026312 10.1055/s-1998-1604 10.1016/j.tetlet.2006.10.126 10.1016/S0040-4020(99)00169-6 10.1016/0006-2952(91)90276-B 10.1016/j.bmc.2006.04.023 10.1139/v82-430 10.1016/S0040-4039(00)61326-6 10.1002/ejoc.200800891 10.1021/jm058200e 10.1038/272583a0 10.1021/jm980138g 10.1021/jo070515+ 10.1021/cr800278z 10.1016/j.tet.2010.12.036 10.1021/jm00392a020 10.1016/S0040-4039(00)99010-5 10.1021/je800662m 10.1128/AAC.40.5.1282 |
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| Keywords | bis-Boc protection Penciclovir (PCV) X5 Mitsunobu reaction 2-amino-6-chloropurine |
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| Notes | 2-amino-6-chloropurine, Mitsunobu reaction, bis-Boc protection, Penciclovir （PCV） Li-yan DAI, Qiu-long SHI, Jing ZHANG, Xiao-zhong WANG, Ying-qi CHEN （Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou 310027, China） 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-l,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. 33-1236/O4 ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 |
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| Snippet | Solubility of 2-amino-6-chloropurine in Mitsunobu solvents could be significantly improved after its exocyclic amino group is protected via... |
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| SubjectTerms | Chains Civil Engineering Classical and Continuum Physics Derivatives Engineering Industrial Chemistry/Chemical Engineering Joining Mechanical Engineering Precursors Purines Solubility Solvents Synthesis |
| 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 |
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