Thiourea-Cu(OTf)<sub>2</sub>/NIS-synergistically promoted stereoselective glycoside formation with 2-azidoselenoglycosides or thioglycosides as donors

Li, Zuowa; Shen, Wenyan; Cao, Changyu; Wang, Zhaoyan; Zhang, Yaosheng; Xue, Weihua

doi:10.1039/d4ob00064a

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob00064a

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Thiourea-Cu(OTf)₂/NIS-synergistically promoted stereoselective glycoside formation with 2-azidoselenoglycosides or thioglycosides as donors

Zuowa Li,

Wenyan Shen,

Changyu Cao

et al.

Abstract: NIS with a catalytic amount of thiourea and Cu(OTf) composes a powerful activator system for 2-azidoselenoglycoside and thioglycoside donors, allowing stereoselective glycosylation of alcoholic receptors to furnish the expected glycosides.

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ZnI2-Mediated cis-Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in cis-Selective Glycosylations

Ishiwata,

Zhong,

Tanaka

et al. 2024

Molecules

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An efficient and versatile glycosylation methodology is crucial for the systematic synthesis of oligosaccharides and glycoconjugates. A direct intermolecular and an indirect intramolecular methodology have been developed, and the former can be applied to the synthesis of medium-to-long-chain glycans like that of nucleotides and peptides. The development of a generally applicable approach for the stereoselective construction of glycosidic bonds remains a major challenge, especially for the synthesis of 1,2-cis glycosides such as β-mannosides, β-L-rhamnosides, and β-D-arabinofuranosides with equatorial glycosidic bonds as well as α-D-glucosides with axial ones. This review introduces the direct formation of cis-glycosides using ZnI2-mediated cis-glycosylations of various constrained glycosyl donors, as well as the recent advances in the development of stereoselective cis-glycosylations.

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ZnI2-Mediated cis-Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in cis-Selective Glycosylations

Ishiwata,

Zhong,

Tanaka

et al. 2024

Molecules

View full text Add to dashboard Cite

show abstract

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Thiourea-Cu(OTf)₂/NIS-synergistically promoted stereoselective glycoside formation with 2-azidoselenoglycosides or thioglycosides as donors

Abstract: NIS with a catalytic amount of thiourea and Cu(OTf) composes a powerful activator system for 2-azidoselenoglycoside and thioglycoside donors, allowing stereoselective glycosylation of alcoholic receptors to furnish the expected glycosides.

Cited by 1 publication

References 49 publications

ZnI2-Mediated cis-Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in cis-Selective Glycosylations

ZnI2-Mediated cis-Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in cis-Selective Glycosylations

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Thiourea-Cu(OTf)2/NIS-synergistically promoted stereoselective glycoside formation with 2-azidoselenoglycosides or thioglycosides as donors

Abstract: NIS with a catalytic amount of thiourea and Cu(OTf) composes a powerful activator system for 2-azidoselenoglycoside and thioglycoside donors, allowing stereoselective glycosylation of alcoholic receptors to furnish the expected glycosides.

Cited by 1 publication

References 49 publications

ZnI2-Mediated cis-Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in cis-Selective Glycosylations

ZnI2-Mediated cis-Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in cis-Selective Glycosylations

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About

Thiourea-Cu(OTf)₂/NIS-synergistically promoted stereoselective glycoside formation with 2-azidoselenoglycosides or thioglycosides as donors