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Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines
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dc.contributor.author | Xie, Jian-bo | |
dc.contributor.author | Luo, Jian | |
dc.contributor.author | Winn, Timothy R. | |
dc.contributor.author | Cordes, David B. | |
dc.contributor.author | Li, Guigen | |
dc.date.accessioned | 2014-09-18T08:31:01Z | |
dc.date.available | 2014-09-18T08:31:01Z | |
dc.date.issued | 2014-03-31 | |
dc.identifier | 145061774 | |
dc.identifier | b745bbac-5180-4aff-b4cd-33c0981b81cc | |
dc.identifier | 000334379200001 | |
dc.identifier | 84898049608 | |
dc.identifier.citation | Xie , J , Luo , J , Winn , T R , Cordes , D B & Li , G 2014 , ' Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines ' , Beilstein Journal of Organic Chemistry , vol. 10 , pp. 746-751 . https://doi.org/10.3762/bjoc.10.69 | en |
dc.identifier.issn | 1860-5397 | |
dc.identifier.other | ORCID: /0000-0002-5366-9168/work/28024032 | |
dc.identifier.uri | https://hdl.handle.net/10023/5442 | |
dc.description | The authors acknowledge the financial support from the NIH (R33DA031860), the Robert A. Welch Foundation (D-1361) and the Jiangsu Innovation Team Program (P. R. China) for their support of this research. They also thank NSF Grant CHE-1048553 and the CRIF program for supporting their NMR facility. | en |
dc.description.abstract | A new approach to the anticancer drug Velcade was developed by performing asymmetric borylation of an imine anchored with a chiral N-phosphinyl auxiliary. Throughout the 7-step synthesis, especially in the imine's synthesis and in the asymmetric borylation reactions, operations and work-up were conducted in simple and easy ways without any column chromatographic purification, which defines the GAP (group-assisted purification) chemistry concept. It was found that the optically pure isomer (dr > 99: 1) can be readily obtained by washing the crude mixture of the asymmetric borylation reaction with hexane; the chiral N-phosphinyl auxiliary can be easily recovered after deprotection is finished. Several other N-phosphinylimines were also investigated for the asymmetric borylation reaction. The absolute configuration of the borylation product was confirmed by single crystal X-ray diffraction analysis. | |
dc.format.extent | 6 | |
dc.format.extent | 445004 | |
dc.language.iso | eng | |
dc.relation.ispartof | Beilstein Journal of Organic Chemistry | en |
dc.subject | Asymmetric borylation | en |
dc.subject | GAP chemistry | en |
dc.subject | Organophosphorous | en |
dc.subject | N-phosphinylimine | en |
dc.subject | Velcade | en |
dc.subject | Imine chemistry | en |
dc.subject | Boronic acids | en |
dc.subject | Amino-acids | en |
dc.subject | Chymotrypsin | en |
dc.subject | Inhibitors | en |
dc.subject | Elastase | en |
dc.subject | Esters | en |
dc.subject | Hydroboration | en |
dc.subject | Aldehydes | en |
dc.subject | Reagents | en |
dc.subject | QD Chemistry | en |
dc.subject.lcc | QD | en |
dc.title | Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines | en |
dc.type | Journal item | en |
dc.contributor.institution | University of St Andrews. School of Chemistry | en |
dc.contributor.institution | University of St Andrews. EaSTCHEM | en |
dc.identifier.doi | https://doi.org/10.3762/bjoc.10.69 | |
dc.description.status | Peer reviewed | en |
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