Potassium haloalkyltrifluoroborate salts: synthesis, application, and reversible ligand replacement with MIDA

Burke, Sarah J.; Gamrat, James M.; Santhouse, Jacqueline R.; Tomares, Dylan T.; Tomsho, John W.

doi:10.1016/j.tetlet.2015.08.012

Cited by 8 publications

(5 citation statements)

References 41 publications

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“…After that, THP deprotection was performed to produce the corresponding primary alcohol nucleosides of series 7 . Synthesis of bromoalkyl potassium trifluoroborate electrophiles 8a – c (propyl, butyl, and pentyl, respectively) have been reported previously by the Tomsho group. , Finally, boronic acid-adefovir analogs were obtained via substitution reactions of bromoalkyl-potassium trifluoroborates ( 8a and 8b) with various alcohol nucleosides ( 7a, 7b, 7c , and commercially available 7d ). In this substitution reaction, K 2 CO 3 was used as a base with tetrabutylammonium bromide (TBAB) as a phase transfer catalyst, and the reaction was heated to 90 °C overnight.…”

Section: Resultsmentioning

confidence: 99%

“…Mass spectra were obtained on a Thermo- Fisher Exactive Orbitrap Mass Spectrometer using Electrospray Ionization. Compounds 8a – c were synthesized using previously reported procedures. , Commercially available nucleosides: 6-chloropurine, 2,6-dichloropurine, 2-amino-6-chloropurine, adenine, thymidine, uridine, stavudine, lamivudine, and emtricitabine were purchased from reputable chemical vendors with purity >99%.…”

Section: Experimental Sectionmentioning

confidence: 99%

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Synthesis of Boron-Containing Nucleoside Analogs

Alhthlol,

Orme,

Jefferis

et al. 2024

J. Org. Chem.

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Over the last century, nucleoside-based therapeutics have demonstrated remarkable effectiveness in the treatment of a wide variety of diseases from cancer to HIV. In addition, boroncontaining drugs have recently emerged as an exciting and fruitful avenue for medicinal therapies. However, borononucleosides have largely been unexplored in the context of medicinal applications. Herein, we report the synthesis, isolation, and characterization of two novel boron-containing nucleoside compound libraries which may find utility as therapeutic agents. Our synthetic strategy employs efficient one-step substitution reactions between a diverse variety of nucleoside scaffolds and an assortment of n-alkyl potassium trifluoroborate-containing electrophiles. We demonstrated that these alkylation reactions are compatible with cyclic and acyclic nucleoside substrates, as well as increasing alkyl chain lengths. Furthermore, regioselective control of product formation can be readily achieved through manipulation of base identity and reaction temperature conditions.

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Section: Resultsmentioning

confidence: 99%

Section: Experimental Sectionmentioning

confidence: 99%

Synthesis of Boron-Containing Nucleoside Analogs

Alhthlol,

Orme,

Jefferis

et al. 2024

J. Org. Chem.

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“…The boron electrophile is synthesized by the hydroboration of 3-bromopropene in an efficient, one-pot method developed in our lab. 38 Boron trichloride and triethyl silane allow the in situ production of dichloroborane for hydroboration. Exposure of this intermediate to water followed by potassium hydrogen fluoride provides for hydrolysis to the boronic acid and subsequent conversion to the trifluoroborate In an attempt to enhance membrane permeability and, potentially, activity against M. smegmatis, we synthesized lipophilic prodrugs of 4 (Scheme 2).…”

Section: ■ Resultsmentioning

confidence: 99%

“…The synthetic route for the γ-borono phosphonate 4 is described in Scheme . The boron electrophile is synthesized by the hydroboration of 3-bromopropene in an efficient, one-pot method developed in our lab . Boron trichloride and triethyl silane allow the in situ production of dichloroborane for hydroboration.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Antimicrobial Evaluation of γ-Borono Phosphonate Compounds in Escherichia coli and Mycobacterium smegmatis

et al. 2019

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Drug resistance in bacteria is a serious threat, and drugs with novel modes of action are constantly needed. Fosmidomycin is a naturally occurring antibiotic that inhibits the nonmevalonate pathway via inhibition of the enzyme 1-deoxylulose-5-phosphate reductoisomerase (DXR). This work is the first report in which a boronic acid is evaluated as an isostere of the retrohydroxamate moiety of fosmidomycin. We report the novel synthesis of a γ-borono phosphonate analog of fosmidomycin and its corresponding prodrugs. We evaluate the inhibition of DXR and the antimicrobial activity of γ-borono phosphonate compounds against Escherichia coli wild type, E. coli Δglycerol-3-phosphate transporter, and Mycobacterium smegmatis. Despite its structural similarities, the γ-borono phosphonate compound shows antimicrobial activity against E. coli with a mechanism of action that is different from fosmidomycin. This was proven with an underutilized method for studying in vitro inhibition of the MEP pathway in E. coli via isopentenyl pyrophosphate chemical rescue. These results indicate that these compounds may serve as a promising scaffold for developing a new class of antimicrobial agents.

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“…Also, the lack of solubility in organic solvents arises as Lewis basic substituents are introduced. In the case of boronic acids, these issues are addressed with a series of trivalent protecting groups such as MIDA boronates, 20 trifluoroborate salts, 21,22 as well as divalent pinacol esters (Bpin) and 1,8-diaminonaphthalene (Bdan) complexes. 23 At this time, there has been only one benzoxaborole protecting group described in the literature: 1-dimethylamino-8-methylaminonaphthalene.…”

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confidence: 99%

Protection of the Benzoxaborole Moiety: Synthesis and Functionalization of Zwitterionic Benzoxaborole Complexes

et al. 2018

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The synthesis and utility of three benzoxaborole protecting groups are reported. These protecting groups improve organic solubility and allow otherwise incompatible reactions (oxidations, substitutions, and mild reductions) to be achieved in the presence of the benzoxaborole moiety. 3-( N, N-Dimethylamino)-1-propanol was determined to be useful in one-step sequences and is readily cleaved upon workup. Two other groups, N-methylsalicylidenimine and 2-[1-(methylimino)ethyl]phenol, are suitable for multistep syntheses. Deprotection with mild aqueous acid allows for chromatography-free isolation of the benzoxaborole in high yields.

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Potassium haloalkyltrifluoroborate salts: synthesis, application, and reversible ligand replacement with MIDA

Cited by 8 publications

References 41 publications

Synthesis of Boron-Containing Nucleoside Analogs

Synthesis of Boron-Containing Nucleoside Analogs

Synthesis and Antimicrobial Evaluation of γ-Borono Phosphonate Compounds in Escherichia coli and Mycobacterium smegmatis

Protection of the Benzoxaborole Moiety: Synthesis and Functionalization of Zwitterionic Benzoxaborole Complexes

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