Synthesis of Methoxy‐Substituted Exocyclic (<i>E</i>)‐ and (<i>Z</i>)‐Unsaturated Methyl Pyranosides and a Study of Their Reactivity towards Lewis Acids

Deleuze, Aurélie; Sollogoub, Matthieu; Blériot, Yves; Marrot, Jérôme; Sînaÿ, Pierre

doi:10.1002/ejoc.200300105

Cited by 7 publications

(1 citation statement)

References 31 publications

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“…The high-valent selenium additives, such as SeO 2 , Na 2 SeO 3 , Na 2 SeO 4 , etc, are highly toxic and are being gradually withdrawn from the market. The low-valent organoselenium additives, such as selenocysteine, selenomethionine etc, − are less toxic, but their high prices caused by tedious synthetic steps restrain their application on a large scale. Selenized glucose can be synthesized via the selenization reaction of glucose in just one step, and the cost is rather low.…”

Section: Introductionmentioning

confidence: 99%

Kilogram-Scale Production of Selenized Glucose

Zhou

Liu³

et al. 2020

Ind. Eng. Chem. Res.

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Selenized glucose is a new product that has recently been used as the starting material for the preparation of seleniumcontaining catalyst, antibacterial agent, and even heavy metal scavenger. It has potentially important market prospects and commercial value. The chemical can be synthesized by the selenization reaction of glucose with NaHSe, which is generated in situ via the reduction of selenium powder with NaBH 4 . In this work, we found that oxygen should be strictly avoided during the synthetic reactions and ethanol was the preferable solvent for obtaining the product in stable powder forms. On the basis of these findings, a production line was built to synthesize selenized glucose in kilogram-scale for the first time.

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Section: Introductionmentioning

confidence: 99%

Kilogram-Scale Production of Selenized Glucose

Zhou

Liu³

et al. 2020

Ind. Eng. Chem. Res.

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Hemicarbasucrose: Turning off the Exoanomeric Effect Induces Less Flexibility

López-Méndez

Cai

Zhang

et al. 2007

Chemistry An Asian Journal

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Hemicarbasucrose, a close congener of sucrose in which the endocyclic oxygen atom of the glucose moiety is replaced by a methylene group was synthesized for the first time. The conformational behaviour of hemicarbasucrose was studied by a combination of molecular mechanics and NMR spectroscopy (J and NOE data). It was shown that the carbadisaccharide populates two distinct conformational families in solution, the normal syn-psi conformation, which is the predominating conformation of the parent natural O-glycoside, and the anti-psi conformation, which has not been detected for the O-disaccharide. Interestingly, the hemicarbasucrose is less flexible than its natural congener.

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Tetrasubstituted C‐Glycosylidenes and C‐Glycosyl Compounds from Di‐ and Monobromo‐Substituted exo‐Glycals

et al. 2011

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Efficient methods for functionalization of readily available exo-glycals have been developed. Sequential palladium-catalysed cross-coupling of dibromo-substituted exo-glycals was first explored and allowed the formation of new disubstituted exo-glycals as single stereoisomers. Bromination of furano-and pyrano-methoxycarbonyl-exo-glycals led to a new series of monobrominated derivatives. These vinylic bro-

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Synthesis of Methoxy‐Substituted Exocyclic (E)‐ and (Z)‐Unsaturated Methyl Pyranosides and a Study of Their Reactivity towards Lewis Acids

Cited by 7 publications

References 31 publications

Kilogram-Scale Production of Selenized Glucose

Kilogram-Scale Production of Selenized Glucose

Hemicarbasucrose: Turning off the Exoanomeric Effect Induces Less Flexibility

Tetrasubstituted C‐Glycosylidenes and C‐Glycosyl Compounds from Di‐ and Monobromo‐Substituted exo‐Glycals

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