Practical synthesis of 4′-selenopurine nucleosides by combining chlorinated purines and ‘armed’ 4-selenosugar

Ishii, Kazuki; Saito–Tarashima, Noriko; Ota, Masashi; Yamamoto, Shigehiro; Okamoto, Yasuko; Tanaka, Yoshiyuki; Minakawa, Noriaki

doi:10.1016/j.tet.2016.08.071

Cited by 13 publications

(16 citation statements)

References 33 publications

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“…In particular, the selenosugar 73 is treated with iodosylbenzene, TMSOTf, 2,6-lutidine and silylated uracile, as reported in Scheme 14 [30]. A similar approach has been recently extended for the synthesis of 4'-selenopurine [31].…”

Section: Selenonucleoside Analogs and Other Organoselenium Compounds mentioning

confidence: 99%

Synthetic Approaches to Organoselenium Derivatives with Antimicrobial and Anti-Biofilm Activity

Leo

Messina²,

Nascimento

et al. 2019

MROC

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In the recent years, an increasing attention has been given to the biological activities exerted by organoselenium compounds. In 1984, Sies reported for the first time the ability of ebselen to mimic the activity of glutathione peroxidase. From this milestone, several studies reported the pharmacological properties of selenium-containing compounds including their exploitation as antimicrobials. In this context, this minireview presents the most recent examples of seleno derivatives endowed with antimicrobial activities while discussing the most interesting and recent synthetic procedures used to obtain these compounds.

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Section: Selenonucleoside Analogs and Other Organoselenium Compounds mentioning

confidence: 99%

Synthetic Approaches to Organoselenium Derivatives with Antimicrobial and Anti-Biofilm Activity

Leo

Messina²,

Nascimento

et al. 2019

MROC

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“…Minakawa’s group attempted to apply the aforementioned reaction to the synthesis of purine derivatives [ 60 ]. Based on the reports by Jeong et al, who synthesized 4’-selenoadenosine using the Vorbrüggen reaction [ 53 ], they conceived that the hypervalent iodine-mediated reaction of “disarmed” sugar donor 73 bearing an electron-withdrawing group at the 2-position would not readily yield the desired purine derivative.…”

Section: Reviewmentioning

confidence: 99%

“…To isomerize the undesired N7-isomer to the desired product as in the case of 2,6-dichloropurine, the subsequent treatment of the resulting mixture with TMSOTf in toluene at 90 °C gave rise to exclusive formation of the desired N9-isomer 81 in 62% yield. Finally, 81 was converted to the desired guanosine derivative 82 [ 60 ] ( Scheme 11 ).…”

Section: Reviewmentioning

confidence: 99%

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

Yoshimura¹,

Wakamatsu²,

Natori³

et al. 2018

Beilstein J. Org. Chem.

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To synthesize nucleoside and oligosaccharide derivatives, we often use a glycosylation reaction to form a glycoside bond. Coupling reactions between a nucleobase and a sugar donor in the former case, and the reaction between an acceptor and a sugar donor of in the latter are carried out in the presence of an appropriate activator. As an activator of the glycosylation, a combination of a Lewis acid catalyst and a hypervalent iodine was developed for synthesizing 4’-thionucleosides, which could be applied for the synthesis of 4’-selenonucleosides as well. The extension of hypervalent iodine-mediated glycosylation allowed us to couple a nucleobase with cyclic allylsilanes and glycal derivatives to yield carbocyclic nucleosides and 2’,3’-unsaturated nucleosides, respectively. In addition, the combination of hypervalent iodine and Lewis acid could be used for the glycosylation of glycals and thioglycosides to produce disaccharides. In this paper, we review the use of hypervalent iodine-mediated glycosylation reactions for the synthesis of nucleosides and oligosaccharide derivatives.

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“…Thus, the authors pursued the use of 40 , a variant of 26 , that had previously been used in a Vorbrüggen coupling with the above-mentioned purines. 25 In this work, the authors were able to isomerize the N 7 “glycosylation” product to the N 9 isomer, using TMSOTf (Scheme 9). …”

Section: Glycosylation-type Reactions Leading To Nucleoside Analoguesmentioning

confidence: 99%

When nucleoside chemistry met hypervalent iodine reagents

Lakshman

Zajc

2017

Arkivoc

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There has been increasing use of hypervalent iodine reagents in the field of nucleoside chemistry. Applications span: (a) synthesis of nucleoside analogues with sulfur and seleno sugar surrogates, (b) synthesis of unusual carbocyclic and ether ring-containing nucleosides, (c) introduction of sulfur and selenium into pyrimidine bases of nucleosides and analogues, (d) synthesis of isoxazole and isoxazoline ring-containing nucleoside analogues, (e) involvement of purine ring nitrogen atoms for remote C–H bond oxidation, and (f) metal-catalyzed and uncatalyzed synthesis of benzimidazolyl purine nucleoside analogues by intramolecular C–N bond formation. This review offers a perspective on developments involving the use of hypervalent iodine reagents in the field of nucleoside chemistry that have appeared in the literature in the 2003–2017 time frame.

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Practical synthesis of 4′-selenopurine nucleosides by combining chlorinated purines and ‘armed’ 4-selenosugar

Cited by 13 publications

References 33 publications

Synthetic Approaches to Organoselenium Derivatives with Antimicrobial and Anti-Biofilm Activity

Synthetic Approaches to Organoselenium Derivatives with Antimicrobial and Anti-Biofilm Activity

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

When nucleoside chemistry met hypervalent iodine reagents

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