Glycosylation Reaction of &lt;i&gt;Thioglycosides&lt;/i&gt; by Using Hypervalent Iodine(III) Reagent as an Excellent Promoter

Kajimoto, Tetsuya; Ogawa, Ryosuke; Dohi, Toshifumi; Kita, Yasuyuki

doi:10.1248/cpb.c16-00203

Cited by 13 publications

(8 citation statements)

References 44 publications

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“…This indicated peracetylated thioglycosides would not be suitable for this glycosidation protocol. This result, however, conforms to the literature where peracetylated thioglycoside donors often preformed less efficiently, compared to perbenzoylated donors . As such, the fully benzoylated thiogalactoside 14 was then used as donor and subjected to the glycosidation reactions with acceptors 3 and 22 , respectively, under the above activation conditions; as expected, the corresponding disaccharides 32 and 33 were generated in very good yields (Table , entries 7 and 8).…”

Section: Resultssupporting

confidence: 88%

N‐Trifluoromethylthiosaccharin/TMSOTf: A New Mild Promoter System for Thioglycoside Activation

2019

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For the first time, N‐trifluoromethylthiosaccharin was used to activate thioglycosides in the presence of catalytic amounts of TMSOTf. The results show that the activated thioglycosides undergo glycosidation reactions with various glycosyl acceptors to give the corresponding glycosides in moderate to excellent yields. In addition, orthogonal activation of ethyl thioglycoside in the presence of phenyl thioglycoside was achieved under the developed conditions.

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Section: Resultssupporting

confidence: 88%

N‐Trifluoromethylthiosaccharin/TMSOTf: A New Mild Promoter System for Thioglycoside Activation

2019

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“…[136][137][138][139][140][141] van Boom and colleagues have reported glycosylation reactions of thioglycosides using a combination of stoichiometric amounts of N-iodosuccinimide and catalytic amounts of triflic acid. 142) Recently, we have reported a novel glycosylation reaction of a thioglycoside using hypervalent iodine(III) as an activator 143,144) (Chart 20).…”

Section: Gycosylation Of Thioglycosidesmentioning

confidence: 99%

Metal-Free Oxidative Cross-Coupling Reaction of Heteroaromatic and Related Compounds

Morimoto

2019

Chem. Pharm. Bull.

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The biary unit having heteroatom as important scaffolds widely exist in a large number of biologically active compounds and functional organic molecules. Since the cross-coupling is a useful synthetic method for constructing biaryl and heterobiaryl structures, the development of novel cross-coupling methods has been studied intensively. The oxidative biaryl coupling reaction of aromatic compounds having heteroatoms is an attractive method since they do not require the prefunctionalization of arenes. This report describes recent advances in hypervalent iodine(III) induced metal-free synthesis of biaryls having heteroatoms.

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“…Recently, the reaction was revisited by Kajimoto et al, who sought a glycosylation reaction that could be applied to disarmed thioglycosides using hypervalent iodine reagents [ 80 – 81 ]. One of the reactions they examined was the glycosylation reaction of methyl 2-phthalimidothioglucopyranoside 153 with methyl tribenzylglucopyranoside 149 by PIFA in the presence of various acid catalysts.…”

Section: Reviewmentioning

confidence: 99%

“…On the other hand, the use of bis[cyclohexyl]trifluoromethanesulfonylborane [(cyclo-Hex) 2 BOTf] and methanesulfonic acid resulted in a poor yield. The synthesis of disaccharides under the optimized conditions was performed using “odorless” thioglycoside 155 and 149 as the donor and the acceptor [ 81 ]. Even with the combination of “disarmed” 155 and “armed” 149 , the reaction gave rise to the desired disaccharide 157 in 87% yield.…”

Section: Reviewmentioning

confidence: 99%

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

Yoshimura¹,

Wakamatsu²,

Natori³

et al. 2018

Beilstein J. Org. Chem.

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To synthesize nucleoside and oligosaccharide derivatives, we often use a glycosylation reaction to form a glycoside bond. Coupling reactions between a nucleobase and a sugar donor in the former case, and the reaction between an acceptor and a sugar donor of in the latter are carried out in the presence of an appropriate activator. As an activator of the glycosylation, a combination of a Lewis acid catalyst and a hypervalent iodine was developed for synthesizing 4’-thionucleosides, which could be applied for the synthesis of 4’-selenonucleosides as well. The extension of hypervalent iodine-mediated glycosylation allowed us to couple a nucleobase with cyclic allylsilanes and glycal derivatives to yield carbocyclic nucleosides and 2’,3’-unsaturated nucleosides, respectively. In addition, the combination of hypervalent iodine and Lewis acid could be used for the glycosylation of glycals and thioglycosides to produce disaccharides. In this paper, we review the use of hypervalent iodine-mediated glycosylation reactions for the synthesis of nucleosides and oligosaccharide derivatives.

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Glycosylation Reaction of <i>Thioglycosides</i> by Using Hypervalent Iodine(III) Reagent as an Excellent Promoter

Cited by 13 publications

References 44 publications

N‐Trifluoromethylthiosaccharin/TMSOTf: A New Mild Promoter System for Thioglycoside Activation

N‐Trifluoromethylthiosaccharin/TMSOTf: A New Mild Promoter System for Thioglycoside Activation

Metal-Free Oxidative Cross-Coupling Reaction of Heteroaromatic and Related Compounds

Glycosylation reactions mediated by hypervalent iodine: application to the synthesis of nucleosides and carbohydrates

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