Cationic gold(<scp>i</scp>)-catalyzed glycosylation with glycosyl <i>N</i>-1,1-dimethylpropargyl carbamate donors

Synthesis of an antigenic tetrasaccharide repeating unit of the Opolysaccharide of Salmonella enteritidis lipopolysaccharide has been accomplished. Those four monosaccharides were assembled stereoselectively by employing our recently developed cationic gold(I)-catalyzed glycosylation methodology involving various glycosyl N-1,1-dimethylpropargyl carbamate donors. The newly formed α-anomeric stereochemical configuration was controlled by the axial C2-OBz of the glycosyl donors via anchimeric assistance.

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

Ding

Lyu

Zhang

et al. 2023

Nat Commun

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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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Cationic gold(i)-catalyzed glycosylation with glycosyl N-1,1-dimethylpropargyl carbamate donors

Abstract: A mild and efficient cationic gold(I)-catalyzed O-glycosylation methodology involving the use of bench-stable glycosyl N-1,1-dimethylpropargyl carbamate donors has been developed. In the presence of 1-2 mol% [tris(2,4-di-tert-butylphenyl)phosphite]gold(I) chloride and 5...

Cited by 4 publications

References 26 publications

Gold(I)-catalyzed rearrangement of glycosyl ortho-allenylbenzoates leading to the formation of C-glycosides

Gold(I)-catalyzed rearrangement of glycosyl ortho-allenylbenzoates leading to the formation of C-glycosides

Synthesis of Salmonella enteritidis Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl N-1,1-Dimethylpropargyl Carbamate Donors

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

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