A Mild Glycosylation Protocol with Glycosyl 1‐Methylimidazole‐2‐carboxylates as Donors

Chen, Jianpeng; Tang, Yu; Yu, Biao

doi:10.1002/ejoc.202100677

Cited by 7 publications

(1 citation statement)

References 77 publications

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“…However, simple glycosyl esters like glycosyl acetates and benzoates have mediocre reactivities and glycosylation reactions employing these donors have narrow acceptor scopes and require the addition of superstoichiometric amounts of promoters 4 , 20 . Donors with certain modified ester leaving groups such as glycosyl pentenoates 21 , glycosyl ortho -(1-phenylninyl)benzoates 22 , glycosyl heteroaromatic carboxylate esters 23 – 25 , and glycosyl allenoates 26 show enhanced reactivities and expanded acceptor scopes, while few catalytic activation methods for glycosyl ester donors are available to date.…”

Section: Introductionmentioning

confidence: 99%

Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho−2,2-dimethoxycarbonylcyclopropylbenzoate donors

et al. 2023

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Catalytic glycosylation is a vital transformation in synthetic carbohydrate chemistry due to its ability to expediate the large-scale oligosaccharide synthesis for glycobiology studies with the consumption of minimal amounts of promoters. Herein we introduce a facile and efficient catalytic glycosylation employing glycosyl ortho−2,2-dimethoxycarbonylcyclopropylbenzoates (CCBz) promoted by a readily accessible and non-toxic Sc(III) catalyst system. The glycosylation reaction involves a novel activation mode of glycosyl esters driven by the ring-strain release of an intramolecularly incorporated donor-acceptor cyclopropane (DAC). The versatile glycosyl CCBz donor enables highly efficient construction of O-, S-, and N-glycosidic bonds under mild conditions, as exemplified by the convenient preparation of the synthetically challenging chitooligosaccharide derivatives. Of note, a gram-scale synthesis of tetrasaccharide corresponding to Lipid IV with modifiable handles is achieved using the catalytic strain-release glycosylation. These attractive features promise this donor to be the prototype for developing next generation of catalytic glycosylation.

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Section: Introductionmentioning

confidence: 99%

Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho−2,2-dimethoxycarbonylcyclopropylbenzoate donors

et al. 2023

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1‐(2’‐Hydroxy‐2’‐Methylpropionyl)Glycoside as a Versatile Glycosyl Donor for O‐/C‐Glycosylation

Liu,

Xiao

et al. 2024

Chemistry A European J

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Herein, we developed a Lewis acid‐mediated O‐glycosylation and C‐glycosylation protocol using stable glycosyl 2′‐hydroxy‐2′‐methylpropionates as donors. These glycosylation reactions reached completion within 1 h at room temperature. The practicality of this protocol is characterized by their straightforward operation and efficient applicability to various substrates, including both disarmed and armed glycosyl donors, through the remote activation of easily accessible TMSOTf.

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Triflic Imide‐Catalyzed Glycosylation of Disarmed Glycosyl ortho‐Isopropenylphenylacetates and ortho‐Isopropenylbenzyl Thioglycosides

Qiao

Wang

et al. 2022

Eur J Org Chem

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Glycosylation reaction involving the coupling of a glycosyl donor with a glycosyl acceptor is one of the cornerstones of chemical preparation of pure glycans and glycoconjugates of biological relevance. Catalytic glycosylation of glycosyl ester donors and thioglycosides is an attractive but underexplored topic in carbohydrate chemistry. Herein, triflic imide (Tf 2 NH)catalyzed glycosylation of various O-, S-, and C-nucleophiles has been achieved using disarmed glycosyl ortho-isopropenylphenylacetates (GIPPAs) and ortho-isopropenylbenzyl thioglycosides as glycosylating agents. The reactions proceed under mild conditions to give the desired glycosides in good-to-excellent yields. Of particular note, the comparable reactivity for the αisomers and the β-ones of GIPPAs is observed. The mechanistic investigation demonstrates that the isopropenyl group is essential for the reaction and its preferential protonation triggers the reaction. This work provides another member to the arsenals of glycosyl ester and thioglycoside donors suitable for acid-catalyzed glycosylation to create various glycosidic bonds.

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A Mild Glycosylation Protocol with Glycosyl 1‐Methylimidazole‐2‐carboxylates as Donors

Cited by 7 publications

References 77 publications

Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho−2,2-dimethoxycarbonylcyclopropylbenzoate donors

Efficient and versatile formation of glycosidic bonds via catalytic strain-release glycosylation with glycosyl ortho−2,2-dimethoxycarbonylcyclopropylbenzoate donors

1‐(2’‐Hydroxy‐2’‐Methylpropionyl)Glycoside as a Versatile Glycosyl Donor for O‐/C‐Glycosylation

Triflic Imide‐Catalyzed Glycosylation of Disarmed Glycosyl ortho‐Isopropenylphenylacetates and ortho‐Isopropenylbenzyl Thioglycosides

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