Ytterbium(iii) Tris[bis(perfluoro-Butylsulfonyl)amide] as a Lewis Acid for Glycosidations

Yamanoi, Takahiro; Nagayama, Sonoe; Ishida, Hideyuki; Nishikido, Joji; Inazu, Toshiyuki

doi:10.1081/scc-100103325

Cited by 19 publications

(4 citation statements)

References 15 publications

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“…In addition to various cyclization, rearrangement, alkylation, and acylation reactions of formation of C–C and C–heteroatom bonds, some other applications of the triflimide metal salts should be mentioned. Thus, Yb(NTf 2 ) 3 and triflimide itself , as well as N -trimethylsilyltriflimide were shown to be good catalysts for glycosidation reactions.…”

Section: Catalysts With Triflamide Moietymentioning

confidence: 99%

Trifluoromethanesulfonamides and Related Compounds

2012

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Section: Catalysts With Triflamide Moietymentioning

confidence: 99%

Trifluoromethanesulfonamides and Related Compounds

2012

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“…Interestingly, complete inversion at the anomeric center was observed in these reactions. Inazu and co-workers showed the activation of glycosyl fluorides in the presence of catalytic amounts of ytterbium(III) tris[bis(perfluorobutylsulfonyl) amide] (Yb[N(O 2 SC 4 F 9 ) 2 ] 3 , 5 mol %) …”

Section: Glycosyl Fluoridesmentioning

confidence: 99%

“…Inazu and co-workers showed the activation of glycosyl fluorides in the presence of catalytic amounts of ytterbium(III) tris[bis(perfluorobutylsulfonyl) amide] (Yb[N(O 2 SC 4 F 9 ) 2 ] 3 , 5 mol %). 484 Other rare earth metals were found to promote the glycosidation of glycosyl fluorides. 481,482 Detailed investigation led to the development of a catalytic activation of glycosyl fluorides with trimethylsilyl ether acceptors.…”

Section: Glycosidation Of Glycosyl Fluoridesmentioning

confidence: 99%

Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century

2022

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Advances in synthetic carbohydrate chemistry have dramatically improved access to common glycans. However, many novel methods still fail to adequately address challenges associated with chemical glycosylation and glycan synthesis. Since a challenge of glycosylation has remained, scientists have been frequently returning to the traditional glycosyl donors. This review is dedicated to glycosyl halides that have played crucial roles in shaping the field of glycosciences and continue to pave the way toward our understanding of chemical glycosylation.

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“…It was furthermore shown that the β-glycosides could be anomerized using SnCl 4 and AgClO 4 in MeNO 2 at rt. A related catalyst, Yb(N(O 2 SC 4 F 9 ) 2 ) 3 , has been investigated by Yamanoi et al for activation of perbenzylated glycosyl esters . In the glycosylation of a 6-OH acceptor, a 68% yield was obtained as a 1:1 mixture of anomers.…”

Section: Glycosyl Esters As Donorsmentioning

confidence: 99%

Catalytic Glycosylations in Oligosaccharide Synthesis

2018

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Catalytic glycosylation has been a central reaction in carbohydrate chemistry since its introduction by Fischer 125 years ago, but it is only in the past three to four decades that catalytic methods for synthesizing oligosaccharides have appeared. Despite the development of numerous elegant and ingenious catalytic glycosylation methods, only a few are in general use. This review covers all methods of catalytic glycosylation with the focus on the development and application in oligosaccharide synthesis and provide an overview of the scope and limitations of these. The review also includes relevant mechanistic studies of catalytic glycosylations. The future of catalytic glycosylation chemistry is discussed, including specific, upcoming methods and possible directions for the field of research in general.

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Ytterbium(iii) Tris[bis(perfluoro-Butylsulfonyl)amide] as a Lewis Acid for Glycosidations

Cited by 19 publications

References 15 publications

Trifluoromethanesulfonamides and Related Compounds

Trifluoromethanesulfonamides and Related Compounds

Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century

Catalytic Glycosylations in Oligosaccharide Synthesis

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