A convergent approach to synthesis of bortezomib: the use of TBTU suppresses racemization in the fragment condensation
Bortezomib is a first-in-class therapeutic antineoplastic agent used for treating patients with multiple myeloma and mantle cell lymphoma. In this paper we report an improved method for synthesis of the title compound using a convergent approach. TBTU was found to efficiently suppress racemization i...
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| Published in | Tetrahedron Vol. 65; no. 34; pp. 7105 - 7108 |
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| Main Authors | , , |
| Format | Journal Article |
| Language | English |
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22.08.2009
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| Abstract | Bortezomib is a first-in-class therapeutic antineoplastic agent used for treating patients with multiple myeloma and mantle cell lymphoma. In this paper we report an improved method for synthesis of the title compound using a convergent approach. TBTU was found to efficiently suppress racemization in the fragment condensation. In comparison with the original synthesis, the presented one is shorter by two steps, higher in yield, and provides better atom economy.
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| AbstractList | Bortezomib is a first-in-class therapeutic antineoplastic agent used for treating patients with multiple myeloma and mantle cell lymphoma. In this paper we report an improved method for synthesis of the title compound using a convergent approach. TBTU was found to efficiently suppress racemization in the fragment condensation. In comparison with the original synthesis, the presented one is shorter by two steps, higher in yield, and provides better atom economy. (C) 2009 Elsevier Ltd. All rights reserved. Bortezomib is a first-in-class therapeutic antineoplastic agent used for treating patients with multiple myeloma and mantle cell lymphoma. In this paper we report an improved method for synthesis of the title compound using a convergent approach. TBTU was found to efficiently suppress racemization in the fragment condensation. In comparison with the original synthesis, the presented one is shorter by two steps, higher in yield, and provides better atom economy. [Display omitted] |
| Author | Shishkov, Sergey V. Ivanov, Andrey S. Zhalnina, Anna A. |
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| Cites_doi | 10.1038/sj.leu.2404528 10.3762/bjoc.4.39 10.1124/dmd.104.002956 10.1002/jlcr.1173 10.1038/nature05569 10.1021/ar00152a002 10.1021/cr00097a009 10.1039/P19790002881 10.1158/1078-0432.CCR-03-0781 10.1016/S0960-894X(98)00029-8 10.1016/S1074-5521(01)00056-4 |
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| Keywords | TBTU Racemization Bortezomib PS-341 Convergent synthesis Peptide coupling PROTEASOME INHIBITORS |
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| SubjectTerms | Bortezomib Chemistry Chemistry, Organic Convergent synthesis Peptide coupling Physical Sciences PS-341 Racemization Science & Technology TBTU |
| Title | A convergent approach to synthesis of bortezomib: the use of TBTU suppresses racemization in the fragment condensation |
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