Using In(III) as a promoter for glycosylation

Mattson, Amanda Lynn; Michel, Anna K.; Cloninger, Mary J.

doi:10.1016/j.carres.2011.10.016

Cited by 15 publications

(9 citation statements)

References 23 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Et 2 O over TMSOTf for the activation of trichloroacetimidate or ( N ‐phenyl)trifluoroacetimidate donors, leading to the selective formation of 1,2‐ trans glycosides in high yields, has been widely studied . However, with more recent studies in 2012, Cloninger and co‐workers have established that In III salts serve as even better and more effective promoters than BF 3 ⋅Et 2 O for performing glycosylations with glycosylacetimidate donors . To establish the novelty of the salts, InCl 3 , InBr 3 , and In(OTf) 3 were reacted with various protecting‐group‐manipulated glycosyltrichloroacetimidate donors, and all of them led to the formation of the glycosylated products in high yields.…”

Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

View full text Add to dashboard Cite

The development of glycobiology relies on the sources of particular oligosaccharides in their purest forms. As the isolation of the oligosaccharide structures from natural sources is not a reliable option for providing samples with homogeneity, chemical means become pertinent. The growing demand for diverse oligosaccharide structures has prompted the advancement of chemical strategies to stitch sugar molecules with precise stereo‐ and regioselectivity through the formation of glycosidic bonds. This Review will focus on the key developments towards chemical O‐glycosylations in the current century. Synthesis of novel glycosyl donors and acceptors and their unique activation for successful glycosylation are discussed. This Review concludes with a summary of recent developments and comments on future prospects.

show abstract

Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

View full text Add to dashboard Cite

show abstract

“…14 It should be noted that InBr 3 and other Lewis acids have been used in conjunction with the O-glycosylation of trichloroacetimidate donors. 15 We have previously reported the catalytic use of InBr 3 14 and other Lewis acids 16 to generate O-glycosides from weakly electrophilic peracetate sugars.…”

mentioning

confidence: 99%

Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis

Szabó

Hanrahan

Jones

et al. 2016

Carbohydrate Research

View full text Add to dashboard Cite

Here we report a method for the preparation of anomerically pure β-S-glycopyranosides (1,2-trans-glycosides) from the corresponding peracetate donors. S-glycosylation was performed in CHCl3 at reflux in the presence of a catalytic amount of InBr3. Deacylation of the intermediate peracetates were achieved under Zemplén conditions. Five pyranose examples, monosaccharides D-glucose and D-galactose and disaccharides cellobiose, maltose, and lactose, were used as donors, and five thiols including an α/ω dithiol and Fmoc-L-cysteine were used as acceptors. Melting points, high res MS, [α]D and NMR data ((1)H and (13)C, including COSY, HSQC and HMBC) are reported for compounds not previously described.

show abstract

“…Mattson et al reported the use of In(III) salts as a catalyst for TCA activation in 2012. During their investigation, InCl 3 , InBr 3 , and In(OTf) 3 were studied as novel catalysts in glycosylations.…”

Section: Glycosyl Imidate Donorsmentioning

confidence: 99%

“…94 In a later publication by the Iadonisi group in 2008, the synthesis of a pentasaccharide was completed in three steps starting from monosaccharide building blocks via Yb(OTf) 3 -and Bi(OTf) 3 catalysis of both TCA and N-phenyl trifluoroacetimidate (PTFA) donors. 106 Mattson et al 107 reported the use of In(III) salts as a catalyst for TCA activation in 2012. During their investigation, InCl 3 , InBr 3 , and In(OTf) 3 were studied as novel catalysts in glycosylations.…”

Section: Trichloroacetimidatesmentioning

confidence: 99%

Catalytic Glycosylations in Oligosaccharide Synthesis

2018

View full text Add to dashboard Cite

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.

show abstract

Using In(III) as a promoter for glycosylation

Cited by 15 publications

References 23 publications

Chemical O‐Glycosylations: An Overview

Chemical O‐Glycosylations: An Overview

Preparation of S-glycoside surfactants and cysteine thioglycosides using minimally competent Lewis acid catalysis

Catalytic Glycosylations in Oligosaccharide Synthesis

Contact Info

Product

Resources

About