Synthesis of Urea‐Tethered Disaccharides in Water

Ichikawa, Yoshiyasu; Matsukawa, Yohei; Tamura, Mari; Ohara, Fumiyo; Isobe, Mitsuaki; Kotsuki, Hiyoshizo

doi:10.1002/asia.200600190

Cited by 16 publications

(6 citation statements)

References 17 publications

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“…During the course of our methodology studies, we became interested in the synthesis of glycosyl ureas because their functionality is increasingly recognized as a biologically relevant moiety . A number of powerful tools have emerged recently for the construction of this functionality. , However, the stereoselective synthesis of α- and β-glycosyl ureas is still lacking. Additionally, glycosyl ureas are generally prepared in several steps starting from glycosyl azides .…”

Section: Resultsmentioning

confidence: 99%

“…A number of powerful tools have emerged recently for the construction of this functionality. , However, the stereoselective synthesis of α- and β-glycosyl ureas is still lacking. Additionally, glycosyl ureas are generally prepared in several steps starting from glycosyl azides . In our methodology studies, glycosyl ureas were formed by dihydroxylation of N -glycosyl trichloroacetamide and subsequent treatment of the resulting diol intermediate with a base and a nitrogen nucleophile (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

“…Therefore, it is desirable to have access to modified structures such as glycosyl ureas that are more stable under biological conditions and still maintain the properties of the natural compounds. There are only a few methods reported, however, for the stereoselective construction of glycosyl urea, and in particular, the stereoselective synthesis of α-glycosyl ureas is still limited. ,, …”

Section: Introductionmentioning

confidence: 99%

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Palladium(II)-Catalyzed Rearrangement of Glycal Trichloroacetimidates: Application to the Stereoselective Synthesis of Glycosyl Ureas

et al. 2008

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The research on the area of glycosyl urea derivatives, in which the O- and N-glycosidic bonds are replaced with the urea-glycosidic linkages, has recently emerged with applications in the field of aminoglycoside antibiotics. We have developed a novel method for the stereoselective synthesis of alpha- and beta-glycosyl ureas via Pd(II)-catalyzed rearrangement of glycal trichloroacetimidates. In our approach, the alpha- and beta-selectivity at the anomeric carbon of N-glycosyl trichloroacetamides depends on the nature of the palladium-ligand catalyst. While the cationic Pd(II)-L-4 (2-trifluoroacetylphenol) complex promotes alpha-selectivity, the neutral Pd(II)-TTMPP-L-5 (4-chloro-2-trifluoroacetylphenol) complex favors beta-selectivity. The resulting alpha- and beta-N-glycosyl trichloroacetamides were further coupled with a diverse array of primary and hindered secondary nitrogen nucleophiles to provide the corresponding glycosyl ureas in moderate to good yields and with no loss of stereochemical integrity at the anomeric carbon. We have further demonstrated the utility of N-glycosyl trichloroacetamides as robust and versatile intermediates in the synthesis of unsymmetrical urea-linked disaccharides and trisaccharide.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Palladium(II)-Catalyzed Rearrangement of Glycal Trichloroacetimidates: Application to the Stereoselective Synthesis of Glycosyl Ureas

et al. 2008

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“…The reaction of 1‐azido‐2‐alcohols with phosphines and CO 2 described by Villarasa and co‐workers has become a common approach towards the synthesis of oxazolidinones 109. Ichikawa’s group applied this strategy to the synthesis of urea‐tethered glycoconjugates (Scheme a) 110,111. For example, a galactopyranosyl azide was reacted with triphenylphosphine and CO 2 to furnish the oxazolidinone product in a two‐step one‐pot sequence.…”

Section: Oxazolidinone Synthesismentioning

confidence: 99%

A High‐Capacity, Low‐Cost Layered Sodium Manganese Oxide Material as Cathode for Sodium‐Ion Batteries

et al. 2014

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A layered sodium manganese oxide material (NaMn3 O5 ) is introduced as a novel cathode materials for sodium-ion batteries. Structural characterizations reveal a typical Birnessite structure with lamellar stacking of the synthetic nanosheets. Electrochemical tests reveal a particularly large discharge capacity of 219 mAh g(-1) in the voltage rang of 1.5-4.7 V vs. Na/Na(+) . With an average potential of 2.75 V versus sodium metal, layered NaMn3 O5 exhibits a high energy density of 602 Wh kg(-1) , and also presents good rate capability. Furthermore, the diffusion coefficient of sodium ions in the layered NaMn3 O5 electrode is investigated by using the galvanostatic intermittent titration technique. The results greatly contribute to the development of room-temperature sodium-ion batteries based on earth-abundant elements.

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“…In 2005, Ichikawa and co-workers described the total synthesis of the glycocinnasperemicin D 29 , a broad-spectrum antibiotic against Gram-negative organisms, which contains two highly functionalised aminosugars connected by an urea linkage [61]. While exploring the synthesis of this target molecule, this group established a new method for the stereoselective synthesis of novel β-urea-linked pseudooligosaccharides, which involves the reaction of amine-glycosides with Steyemark-type gluco- and galactopyranosyl oxazolidinones [62–63]. …”

Section: Reviewmentioning

confidence: 99%

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

Blanco¹,

Ortega‐Caballero²,

Fernández³

2010

Beilstein J. Org. Chem.

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SummaryOligosaccharides are currently recognised as having functions that influence the entire spectrum of cell activities. However, a distinct disadvantage of naturally occurring oligosaccharides is their metabolic instability in biological systems. Therefore, much effort has been spent in the past two decades on the development of feasible routes to carbohydrate mimetics which can compete with their O-glycosidic counterparts in cell surface adhesion, inhibit carbohydrate processing enzymes, and interfere in the biosynthesis of specific cell surface carbohydrates. Such oligosaccharide mimetics are potential therapeutic agents against HIV and other infections, against cancer, diabetes and other metabolic diseases. An efficient strategy to access this type of compounds is the replacement of the glycosidic linkage by amide or pseudoamide functions such as thiourea, urea and guanidine. In this review we summarise the advances over the last decade in the synthesis of oligosaccharide mimetics that possess amide and pseudoamide linkages, as well as studies focussing on their supramolecular and recognition properties.

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Synthesis of Urea‐Tethered Disaccharides in Water

Cited by 16 publications

References 17 publications

Palladium(II)-Catalyzed Rearrangement of Glycal Trichloroacetimidates: Application to the Stereoselective Synthesis of Glycosyl Ureas

Palladium(II)-Catalyzed Rearrangement of Glycal Trichloroacetimidates: Application to the Stereoselective Synthesis of Glycosyl Ureas

A High‐Capacity, Low‐Cost Layered Sodium Manganese Oxide Material as Cathode for Sodium‐Ion Batteries

(Pseudo)amide-linked oligosaccharide mimetics: molecular recognition and supramolecular properties

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