Incorporation of the pentafluorosulfanyl group through common synthetic transformations

Hiscocks, HG; Yit, DL; Pascali, G; Ung, AT

Incorporation of the pentafluorosulfanyl group through common synthetic transformations

Hiscocks, HG Yit, DL Pascali, G Ung, AT

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Publisher:: SPRINGER WIEN
Publication Type:: Journal Article
Citation:: Monatshefte fur Chemie, 2021, 152, (4), pp. 449-459
Issue Date:: 2021-04-01

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Field	Value	Language
dc.contributor.author	Hiscocks, HG
dc.contributor.author	Yit, DL
dc.contributor.author	Pascali, G
dc.contributor.author	Ung, AT
dc.date.accessioned	2022-03-28T00:39:06Z
dc.date.available	2022-03-28T00:39:06Z
dc.date.issued	2021-04-01
dc.identifier.citation	Monatshefte fur Chemie, 2021, 152, (4), pp. 449-459
dc.identifier.issn	0026-9247
dc.identifier.issn	1434-4475
dc.identifier.uri	http://hdl.handle.net/10453/155625
dc.description.abstract	The incorporation of –SF5 group onto model amino acids has been achieved using commercially available synthons substituted with this group. This work investigates the influence of the –SF5 group on a variety of common synthetic transformations utilized in fields of bioconjugation and drug development, namely, amide coupling, reductive amination, diazo-coupling, and CuAAC “click” reactions. The influence of the novel substituent on the success of these common transformations is presented, and alternative approaches for those which proved unsatisfactory are proposed herein. Graphic abstract: [Figure not available: see fulltext.]
dc.language	English
dc.publisher	SPRINGER WIEN
dc.relation.ispartof	Monatshefte fur Chemie
dc.relation.isbasedon	10.1007/s00706-021-02760-4
dc.rights	info:eu-repo/semantics/closedAccess
dc.subject	03 Chemical Sciences
dc.subject.classification	General Chemistry
dc.title	Incorporation of the pentafluorosulfanyl group through common synthetic transformations
dc.type	Journal Article
utslib.citation.volume	152
utslib.for	03 Chemical Sciences
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Science
pubs.organisational-group	/University of Technology Sydney/Faculty of Science/School of Mathematical and Physical Sciences
pubs.organisational-group	/University of Technology Sydney/Strength - CCET - Centre for Clean Energy Technology
utslib.copyright.status	closed_access	*
dc.date.updated	2022-03-28T00:39:03Z
pubs.issue	4
pubs.publication-status	Published
pubs.volume	152
utslib.citation.issue	4

Abstract:

The incorporation of –SF5 group onto model amino acids has been achieved using commercially available synthons substituted with this group. This work investigates the influence of the –SF5 group on a variety of common synthetic transformations utilized in fields of bioconjugation and drug development, namely, amide coupling, reductive amination, diazo-coupling, and CuAAC “click” reactions. The influence of the novel substituent on the success of these common transformations is presented, and alternative approaches for those which proved unsatisfactory are proposed herein. Graphic abstract: [Figure not available: see fulltext.]

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http://hdl.handle.net/10453/155625