New thioglycoside derivatives for use in odourless synthesis of MUXF3 N-glycan fragments related to food allergens

Synthesis of the C-glycosidic analogue 9 of adenophostin A, a very potent IP3 receptor agonist, and its uracil congener 10 was achieved via a temporary silicon-tethered radical coupling reaction as the key step. Phenyl 3,4,6-tri-O-(p-methoxybenzyl)-1-seleno-β-d-glucopyranoside (27) and 3-deoxy-3-methylene-1,2-O-isopropylidene-α-d-erythro-pentofuranose (30) were connected by a dimethylsilyl tether to give the radical coupling reaction substrate 24, which was successively treated with Bu3SnH/AIBN in benzene and TBAF in THF to give the coupling product 25 with the desired (3α,1'α)-configuration as the major product. From 25, the targets 9 and 10 were synthesized via introduction of adenine or uracil base by Vorbrüggen's method and phosphorylation of the hydroxyls by the phosphoramidite method.

Glycosidic bond

Phosphoramidite

Uracil

Coupling reaction

Trisaccharide

10.1021/jo0001333

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Citations (32)

A ratiometric fluorescent probe based on monochlorinated BODIPY for the discrimination of thiophenols over aliphatic thiols in water samples and in living cells

Sensors and Actuators B Chemical (2017)

Xueliang Liu Li‐Ya Niu Yu‐Zhe Chen Yunxu Yang Qing‐Zheng Yang

Thiophenol

BODIPY

10.1016/j.snb.2017.05.176

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Citations (35)

Thiophenol promoted cyclization of enynes

Tetrahedron Letters (1987)

Chris A. Broka David E. Reichert

Thiophenol

10.1016/s0040-4039(01)81027-3

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Citations (51)

Selective and Rapid Detection of Thiophenol by a Novel Fluorescent Probe with Cellular Imaging

Analytical Letters (2022)

Chaoyan Chen Hao Chen Yu‐Shun Yang Hai‐Liang Zhu

Among sulfur-containing species, thiophenol (PhSH) is highly toxic but is uncommonly studied. Here a novel probe is reported for thiophenol with rapid response and high selectivity. Thiophenol was easily distinguished by this probe from other sulfur-containing species including anions and biothiols. The probe was employed for the determination of thiophenol in several buffer systems and in living cells, demonstrating suitability for future work.

Thiophenol

10.1080/00032719.2022.2069794

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Citations (3)

A highly sensitive fluorescence probe for thiophenol in living cells via a substitution-cyclization strategy

Tetrahedron (2019)

Linlin Yang Yang Liu Yan‐Ping Li Hao Wang Haihua Zhang

Thiophenol

10.1016/j.tet.2019.130538

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Citations (10)

The role of thiophenol in the proposed mechanism for one pot transformation of 2-phenylthio-3-aminocyclohexanols to dehydropiperidine derivatives

Arabian Journal of Chemistry (2011)

Firouzeh Nemati Ali Amoozadeh

This paper describes the effect of thiophenol concentration on photochemical rearrangement of 2-phenylthio-3-aminocyclohexanols to the corresponding protected aminoaldehydes. The obtained aminoaldehyde is in equilibrium with its corresponding deoxyazasugar. The latter could be converted to the corresponding dehydropiperidine with a good yield in the same reaction media by controlling the thiophenol concentration. Also a proposed mechanism for this one pot transformation is reported.

Thiophenol

10.1016/j.arabjc.2011.10.014

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Citations (1)

Studies on benzimidazoles. Part IV. Nucleophilic displacement of N-substituted 2-halogenobenzimidazoles by thiophenol

Journal of the Chemical Society B Physical Organic (1968)

Andrea Ricci P. Vivarelli

2-Halogenobenzimidazoles react with thiophenol as well as with benzenethiolate ion. The reaction also occurs in acidic medium. The effect on the reaction of structural modifications in the benzimidazole and in the thiophenol have been investigated. The general kinetic equation Rate =k1[B][ArS–]+k2[BH+][ArSH]+k3[BH+][ArS–] is proposed to explain the overall reaction.

Thiophenol

Benzimidazole

10.1039/j29680001280

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Citations (1)