2015
DOI: 10.1002/ejoc.201500255
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The Development of a Versatile Trifunctional Scaffold for Biological Applications

Abstract: We describe the synthesis of a trifunctional scaffold constructed from a planar core of trimesic acid derivatized with three propargylamine moieties. The scaffold was attached to a solid‐phase resin through the carboxylic group of a fluorinated alkyl spacer arm. The orthogonal protection of two of the alkyne groups with triethylsilyl and triisopropylsilyl moieties enabled modular and efficient derivatization of the scaffold with three different azides by using solid‐phase synthesis on amphiphilic ChemMatrix re… Show more

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Cited by 27 publications
(39 citation statements)
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“…We synthesized scaffold 2 in solution from diamide 3, which was prepared as previously described [4] (Scheme 2). During the amide coupling of diamide 3 and Fmoc-hydrazine [7], using conditions used for the synthesis of scaffold 1 (i.e., PyBrop, DMF, and TEA), we observed the partial deprotection of the Fmoc-hydrazide moiety.…”
Section: Synthesis In Solution: Preparation Of Scaffoldmentioning
confidence: 99%
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“…We synthesized scaffold 2 in solution from diamide 3, which was prepared as previously described [4] (Scheme 2). During the amide coupling of diamide 3 and Fmoc-hydrazine [7], using conditions used for the synthesis of scaffold 1 (i.e., PyBrop, DMF, and TEA), we observed the partial deprotection of the Fmoc-hydrazide moiety.…”
Section: Synthesis In Solution: Preparation Of Scaffoldmentioning
confidence: 99%
“…Synthesis of scaffold 2. Reaction conditions: for the synthesis of 3 (steps (a,b)), refer to our previous report [4]; (c) Fmoc-hydrazine, DIPEA, PyBroP, ACN, 60 °C, 3 h, 57%-67%; (d) 50% TFA/DCM (v/v), r.t., 1 h, 87%-91%.…”
Section: Synthesis In Solution: Preparation Of Scaffoldmentioning
confidence: 99%
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