Synthesis of seleno-carbohydrates derived from d-galactose

Braga, Hugo C.; Wouters, Angélica Terezinha Barth; Zerillo, Felipe B; Lüdtke, Diogo S.

doi:10.1016/j.carres.2010.08.019

Cited by 30 publications

(19 citation statements)

References 53 publications

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“…The 1,6‐diglycosyl diselenide 2 was obtained by reacting 4 with in situ generated 6‐selenogalactose derivative 27 . Complete conversion could not be achieved and formation of symmetrical diselenides 28 and 19 as byproducts was observed (Scheme , Supporting Information).…”

Section: Resultsmentioning

confidence: 99%

Exploring the Syntheses of Novel Glycomimetics. Carbohydrate Derivatives with Se‐S‐ or Se‐Se‐ Glycosidic Linkages

et al. 2016

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A convenient route to Se-S-glycoside derivatives was developed using glycosyl isoselenuronium salts as glycosylselenenyl transfer reagents toward thiols. Aliphatic and aromatic thiols were found to react in the presence of N,N-diisopropylethylamine as a base and furnished alkyl-or aryl glycosylselenenylsulfide derivatives. S-glycosylselenenyl-cysteines were obtained similarly via reactions with O,N-protected cysteine. Reactions with monosaccharide thiols provided dis-accharide mimics featuring Se-S-interglycosidic bonds. Further disaccharide mimics with Se-Se interglycosidic linkage were obtained from the starting isoselenuronium salts via reactions with protected monosaccharide derivatives bearing selenol groups in 6-or 4-position. The novel glycomimetics are expected to open new perspectives in biological activities and/or mechanistic studies due, i.a., to the rather uncommon Se-S-or Se-Se bonds incorporated into a carbohydrate framework.[a] Dr.

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Section: Resultsmentioning

confidence: 99%

Exploring the Syntheses of Novel Glycomimetics. Carbohydrate Derivatives with Se‐S‐ or Se‐Se‐ Glycosidic Linkages

et al. 2016

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“…Interestingly, the potassium salt 66 was further evolved into the diselenides 67 [ 72 ], valuable compounds per se, but also precursors of nucleophilic ( Scheme 10 ), electrophilic [ 73 ], or radical selenium-centered reagents [ 74 ]. Sugar diselenides were awfully prepared by Braga and Ludtke using Li 2 Se 2 as selenylating agent [ 75 , 76 ].…”

Section: Selenoglycosidesmentioning

confidence: 99%

Sweet Selenium: Synthesis and Properties of Selenium-Containing Sugars and Derivatives

et al. 2020

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In the last decades, organoselenium compounds gained interest due to their important biological features. However, the lack of solubility, which characterizes most of them, makes their actual clinical exploitability a hard to reach goal. Selenosugars, with their intrinsic polarity, do not suffer from this issue and as a result, they can be conceived as a useful alternative. The aim of this review is to provide basic knowledge of the synthetic aspects of selenosugars, selenonium salts, selenoglycosides, and selenonucleotides. Their biological properties will be briefly detailed. Of course, it will not be a comprehensive dissertation but an analysis of what the authors think is the cream of the crop of this interesting research topic.

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“…First, the independent synthesis of diselenide 27, the expected product of the air oxidation of 4, was conducted. The homogeneous product was prepared by the reaction of mesylate 1 with dilithium diselenide (Li 2 Se 2 ) 19 affording compound 27 in 88% yield (Scheme 3). The same compound containing inseparable unknown byproducts, may also be obtained by the oxidation of selenol 4 with hydrogen peroxide in the presence of NaOH (79%) and from the equimolar mixture of selenocyanide 3 and selenol 4 in the presence of a base (94%) according to Krief's method.…”

Section: Resultsmentioning

confidence: 99%

“…[α] 20 D 160.5 (c 0.2, chloroform); ν max (film): 2942,2867,1729,1451,1280,1261,1108,1087,1069,1027,757, 710 cm −1 . 1 H NMR (CDCl 3 ) δ: 6.23 (d,1 H,J 5.2 Hz, 8, 79.0, 69.6, 69.5, 69.3, 62.5 (C-5′), 55.3 (C-5), 50.5, 49.9, 47.2, 46.8 (C), 42.5 (C), 40.8 (C), 38.9 (C), 38.7 (CH 2 ), 37.2 (C), 37.0, 35.3 (CH 2 ), 34.2 (CH 2 ), 30.6 (CH 2 ), 29.9 (CH 2 ), 29.0 (CH 2 ), 28.0, 27.4 (CH 2 ), 27.2 (CH 2 ), 25.1 (CH 2 ), 20.9 (CH 2 ), 19.3, 18.5 (CH 2 ), 18.3 (CH 2 ), 16.1,16.0,15.4, 28a-Se-(2,3,4-Tri-O-benzoyl-α-L-arabinopyranosyl)-28a-seleno-28a-homolup-20(29)-en-3β-ol (19). Starting from 12 (110 mg, 0.109 mmol) the title compound was obtained (66 mg, 63%).…”

Section: General Procedures For the Deallylation Reactionmentioning

confidence: 99%

Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins

et al. 2016

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A practical synthesis of 28a-homo-28a-selenolupane triterpenes and the corresponding selenosaponins containing d-mannose, l-arabinose, l-rhamnose, and d-idose moieties is described. Selenium containing triterpenes were obtained from the readily available 3-O-allyl-homobetulin mesylate by nucleophilic substitution with the selenocyanate ion which upon reduction of the -SeCN group afforded the free selenol. Glycosylation using classical Schmidt donors gave 1,2-trans selenosaponins as the main product as well as minute amounts of 1,2-cis isomers. This is one of the very few examples of the synthesis of selenoglycosides by direct glycosylation of free selenols. The studied selenol showed high resistance to air oxidation resulting in good stability during the synthesis of selenolupane derivatives. Cytotoxic activities of new homoselenolupane derivatives were also evaluated in vitro and revealed that some triterpenes exhibited an interesting profile against human cancer cell lines.

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Synthesis of seleno-carbohydrates derived from d-galactose

Cited by 30 publications

References 53 publications

Exploring the Syntheses of Novel Glycomimetics. Carbohydrate Derivatives with Se‐S‐ or Se‐Se‐ Glycosidic Linkages

Exploring the Syntheses of Novel Glycomimetics. Carbohydrate Derivatives with Se‐S‐ or Se‐Se‐ Glycosidic Linkages

Sweet Selenium: Synthesis and Properties of Selenium-Containing Sugars and Derivatives

Synthesis of 28a-homoselenolupanes and 28a-homoselenolupane saponins

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