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dc.contributor.advisorSieburth, Scott McNeill
dc.creatorBo, Yingjian
dc.date.accessioned2020-10-21T14:26:45Z
dc.date.available2020-10-21T14:26:45Z
dc.date.issued2012
dc.identifier.other864885975
dc.identifier.urihttp://hdl.handle.net/20.500.12613/821
dc.description.abstractDialkylsilanediols are a novel class of non-hydrolyzable analogues of the tetrahedral intermediate of amide hydrolysis, shown to be good inhibitors of HIV-1 protease, angiotensin converting enzyme (ACE), and thermolysin. An impediment to utilization of these silanediol structures, however, has been the methods for their assembly. This research describes the reductive lithiation of hydridosilanes and alkoxysilanes, and the use of the resulting silyl anions to develop efficient methods to synthesize silanediol precursors. In the first part of research, lithiation of hydridosilanes was studied. As part of this study, a simple 1H NMR method was developed for monitoring and analyzing the progress of lithiation. In addition, this method was converted to a titration for silyllithium reagents using BHT as an internal standard. Silanediols 107 and 177 are analogues of a potent chymase inhibitor, NK-3201 (82). In the second part, diphenylsilanes 108 and 170, precursors to silanediols 107 and 177, were synthesized using addition of silyllithium to sulfinimine 113 as a key step. In the third part, lithiation of alkoxysilanes was studied. (Si,O)-Dianions, generated from lithiation of silane alcohol 175 or 2,2-diphenyl-1-oxa-2-silacyclopentane (225), were reacted with a wide variety of electrophiles to give potentially useful silicon-containing building blocks. Addition of the (Si,O)-dianion 284 to sulfinimines gave silanediol inhibitor precursors with full control of stereochemistry. In the last part, a new method featuring 1,1-diphenyl-2-azaallyllithium chemistry were utilized to synthesize a series of protected α-amino silanes 323, 329 - 331.
dc.format.extent371 pages
dc.language.isoeng
dc.publisherTemple University. Libraries
dc.relation.ispartofTheses and Dissertations
dc.rightsIN COPYRIGHT- This Rights Statement can be used for an Item that is in copyright. Using this statement implies that the organization making this Item available has determined that the Item is in copyright and either is the rights-holder, has obtained permission from the rights-holder(s) to make their Work(s) available, or makes the Item available under an exception or limitation to copyright (including Fair Use) that entitles it to make the Item available.
dc.rights.urihttp://rightsstatements.org/vocab/InC/1.0/
dc.subjectChemistry
dc.subjectChemistry, Organic
dc.subjectChymase Inhibitor
dc.subjectLithiation of Alkoxysilanes and Hydridosilanes
dc.subjectNk3201
dc.subjectOrganosilane
dc.subjectSilanediol
dc.subjectSulfinimine
dc.titleMethods in organosilane assembly
dc.typeText
dc.type.genreThesis/Dissertation
dc.contributor.committeememberAndrade, Rodrigo B.
dc.contributor.committeememberDavis, Franklin A.
dc.contributor.committeememberCannon, Kevin C.
dc.description.departmentChemistry
dc.relation.doihttp://dx.doi.org/10.34944/dspace/803
dc.ada.noteFor Americans with Disabilities Act (ADA) accommodation, including help with reading this content, please contact scholarshare@temple.edu
dc.description.degreePh.D.
refterms.dateFOA2020-10-21T14:26:45Z


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