Acetolysis of 6‐Deoxysugar Disaccharide Building Blocks: <i>exo</i> versus <i>endo</i> Activation

Cirillo, Luigi; Bedini, Emiliano; Parrilli, Michelangelo

doi:10.1002/ejoc.200800696

Cited by 9 publications

(1 citation statement)

References 41 publications

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“…''MALDI'' used when instrument not specified. (Cirillo, et al, 2008) Benzoate methanolysis catalyzed by α-cyclosophorohexadecaose isolated from Xanthomonas oryzae TOF (DHB) Bradyrhizobial cyclic β-(1→3),(1→6)-glucans as chiral additives for enantiomeric separation of flavanones, by CE TOF (DHB) (Kwon, et al, 2007a) Cyclosophorohexadecaose and succinoglycan monomers as catalytic carbohydrates for the Strecker reaction TOF (DHB) (Lee, et al, 2007f) Hydrolysis of digoxin catalysed by cyclodextrin dicyanohydrins TOF (Bjerre, et al, 2008) Selective acetolysis of 6-deoxy-sugar oligosaccharide building blocks MALDI …”

Section: R-tof (Dhb)mentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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This review is the fifth update of the original review, published in 1999, on the application of MALDI mass spectrometry to the analysis of carbohydrates and glycoconjugates and brings coverage of the literature to the end of 2008. The first section of the review covers fundamental studies, fragmentation of carbohydrate ions, use of derivatives and new software developments for analysis of carbohydrate spectra. Among newer areas of method development are glycan arrays, MALDI imaging and the use of ion mobility spectrometry. The second section of the review discusses applications of MALDI MS to the analysis of different types of carbohydrate. Specific compound classes that are covered include carbohydrate polymers from plants, N- and O-linked glycans from glycoproteins, biopharmaceuticals, glycated proteins, glycolipids, glycosides and various other natural products. There is a short section on the use of MALDI mass spectrometry for the study of enzymes involved in glycan processing and a section on the use of MALDI MS to monitor products of the chemical synthesis of carbohydrates with emphasis on carbohydrate-protein complexes and glycodendrimers. Corresponding analyses by electrospray ionization now appear to outnumber those performed by MALDI and the amount of literature makes a comprehensive review on this technique impractical. However, most of the work relating to sample preparation and glycan synthesis is equally relevant to electrospray and, consequently, those proposing analyses by electrospray should also find material in this review of interest.

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Section: R-tof (Dhb)mentioning

confidence: 99%

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Harvey

2011

Mass Spectrometry Reviews

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Bu₄NI‐Catalyzed CO Bond Formation by Using a Cross‐Dehydrogenative Coupling (CDC) Reaction

Chen

Shi

Liu

et al. 2011

Chemistry A European J

277

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The cleavage and functionalization of CÀH bonds is of fundamental interest for both academia and industry. Generally, the transformation relies on transition metals, [1] which are involved in four major approaches: 1) electrophilic activation of the C À H bond by a high-valent transition metal; 2) oxidative addition to the C À H bond by low-valent transition metals; 3) C À H bond activation by s-bond metathesis, and 4) insertion of a metal carbenoid/nitrenoid into the CÀ H bond. After extensive studies, transition-metal-catalyzed CÀH activation has arisen as an excellent synthetic method to build complex structures because it reduces prefunctionalization while improving atom economy and energy efficiency. However, the use of expensive metal catalysts and the problems involved in removing the residual metals from the final products, which is usually a difficult and tedious process, limits the practical applications of this strategy. The discovery of an efficient CÀH transformation that does not require a metal catalyst would be of great value. This strategy would eliminate the requirement to remove traces of metal from the final products and solve the problem of disposal of the metal catalyst from the reaction mixtures. Recently, several groups disclosed a variety of novel C À C bond formations by using CÀH activation under transition-metalfree conditions. [2,3] The cross-dehydrogenative coupling (CDC) reaction, beyond traditional cross-couplings, has been the object of increasing interest over the last ten years. However, transition-metal catalysts, such as iron and copper salts, were usually required to promote this transformation. [4,5]

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Copper‐Catalyzed Formation of C–O Bonds by Oxidative Coupling of Benzylic Alcohols with Ethers

et al. 2014

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Acetolysis of 6‐Deoxysugar Disaccharide Building Blocks: exo versus endo Activation

Cited by 9 publications

References 41 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Bu₄NI‐Catalyzed CO Bond Formation by Using a Cross‐Dehydrogenative Coupling (CDC) Reaction

Copper‐Catalyzed Formation of C–O Bonds by Oxidative Coupling of Benzylic Alcohols with Ethers

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Acetolysis of 6‐Deoxysugar Disaccharide Building Blocks: exo versus endo Activation

Cited by 9 publications

References 41 publications

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for 2007–2008

Bu4NI‐Catalyzed CO Bond Formation by Using a Cross‐Dehydrogenative Coupling (CDC) Reaction

Copper‐Catalyzed Formation of C–O Bonds by Oxidative Coupling of Benzylic Alcohols with Ethers

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Bu₄NI‐Catalyzed CO Bond Formation by Using a Cross‐Dehydrogenative Coupling (CDC) Reaction