Remarkably efficient activation of glycosyl trichloro- and (N-phenyl)trifluoroacetimidates with bismuth(III) triflate

Adinolfí, Matteo; Iadonisi, Alfonso; Ravidà, Alessandra; Valerio, Silvia

doi:10.1016/j.tetlet.2006.02.034

Cited by 32 publications

(19 citation statements)

References 22 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…[19] Consistently with that report, the reaction proceeded at low temperature to yield the target disaccharide 8 in high yield despite the sterically encumScheme 2. Synthesis of the disaccharide donor of mannopeptimycin ε: Reagents and conditions: a) PhMe/1,2-DME (2:1), Bi(OTf) 3 (cat.)…”

Section: Resultssupporting

confidence: 84%

Synthesis of the Mannopeptimycin Disaccharide and Its Conjugation with 4‐Alkylidene‐β‐lactams

et al. 2008

Self Cite

View full text Add to dashboard Cite

The disaccharide moiety of the antibiotic mannopeptimycin has been synthesized as a (N‐phenyl)trifluoroacetimidate donor, the reactivity of which was tested in conjugation with a 4‐alkylidene‐β‐lactam acceptor. Key steps of the synthesis were Bi(OTf)3‐catalyzed glycosidations that proceeded in short times and with high yields and stereocontrol. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

show abstract

Section: Resultssupporting

confidence: 84%

Synthesis of the Mannopeptimycin Disaccharide and Its Conjugation with 4‐Alkylidene‐β‐lactams

et al. 2008

Self Cite

View full text Add to dashboard Cite

show abstract

“…19,21 A number of other approaches for the synthesis of HOFox have been developed. 22,23 O -Imidates can be activated for glycosylation in the presence of catalytic amounts of TMSOTf, 24,25 BF 3 ·Et 2 O, 26 p -TsOH, 27 Bi(OTf) 3 , 28 Yb(OTf) 3 , 29 Sm(OTf) 3 , 29 AgOTf, 30 or MeOTf. 18 For the further expansion of the regenerative glycosylation reaction we chose TMSOTf, which is arguably the most commonly used promoter.…”

Section: Resultsmentioning

confidence: 99%

Regenerative Glycosylation

et al. 2017

View full text Add to dashboard Cite

Previously, we communicated 3,3-difluoroxindole (HOFox)-mediated glycosylations wherein 3,3-difluoro-3H-indol-2-yl (OFox) imidates were found to be key intermediates. Both the in situ synthesis from the corresponding glycosyl bromides and activation of the OFox imidates could be conducted in a regenerative fashion. Herein, we extend this study to the synthesis of various glycosidic linkages using different sugar series. The main outcome of this study relates to enhanced yields and/or reduced reaction times of glycosylations. The effect of HOFox-mediated reactions is particularly pronounced in case of unreactive glycosyl donors and/or glycosyl acceptors. A multistep regenerative synthesis of oligosaccharides is also reported.

show abstract

“…Two representative Lewis acid catalyzed PTFA glycosidation reactions are shown in Scheme 12. Some other activation systems, such as I 2 / Et 3 SiH, [151] Bi(OTf) 3 , [175] and TMSB(C 6 F 5 ) 4 , [176] have been used to promote PTFA glycosidation reactions. The different reactivity of PTFA and trichloroacetimidate donors was exploited to develop a one-pot multistep procedure featuring the selective activation of a trichloroacetimidate donor in the presence of a PTFA moiety.…”

Section: O-glycosyl Imidates With Electron-withdrawing Groupsmentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

View full text Add to dashboard Cite

Increased understanding of the important roles that oligosaccharides and glycoconjugates play in biological processes has led to a demand for significant amounts of these materials for biological, medicinal, and pharmacological studies. Therefore, tremendous effort has been made to develop new procedures for the synthesis of glycosides, whereby the main focus is often the formation of the glycosidic bonds. Accordingly, quite a few review articles have been published over the past few years on glycoside synthesis; however, most are confined to either a specific type of glycoside or a specific strategy for glycoside synthesis. In this Review, new principles for the formation of glycoside bonds are discussed. Developments, mainly in the last ten years, that have led to significant advances in oligosaccharide and glycoconjugate synthesis have been compiled and are evaluated.

show abstract

Remarkably efficient activation of glycosyl trichloro- and (N-phenyl)trifluoroacetimidates with bismuth(III) triflate

Cited by 32 publications

References 22 publications

Synthesis of the Mannopeptimycin Disaccharide and Its Conjugation with 4‐Alkylidene‐β‐lactams

Synthesis of the Mannopeptimycin Disaccharide and Its Conjugation with 4‐Alkylidene‐β‐lactams

Regenerative Glycosylation

New Principles for Glycoside‐Bond Formation

Contact Info

Product

Resources

About