Hg(OTf)2-catalyzed glycosylation using alkynoate as the leaving group

Imagawa, Hiroshi; Kinoshita, Atsushi; Fukuyama, Takashi; Yamamoto, Hirofumi; Nishizawa, Masatoyo

doi:10.1016/j.tetlet.2006.04.114

Cited by 64 publications

(29 citation statements)

References 43 publications

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“…The mild iodine was also capable of selectively activating these donors over thioglycosides, which helped in performing various sequential glycosylations (Scheme ). Activation of alkynoate glycosides using Hg(OTf) 2 as the promoter has also been reported.…”

Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

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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.

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Section: Glycosylationsmentioning

confidence: 99%

Chemical O‐Glycosylations: An Overview

2016

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“…Since no single method is universally applicable and able to address all the issues associated with glycoside-bond formation, many other glycosyl donors, such as telluroglycosides, [130] glycosyl carbonates, [131] various heteroaryl glycosides, [15,[21][22][23][24][25]132] various N-substituted glycosyl carbamates, [133] methyl 3,5-dinitrosalicylate (DISAL) glycosides, [134,135] glycosyl disulfides, [136] glycosyl sulfimides, [137] N-glycosyl amides, [138] glycosyl phthalates, [139] 2-allyloxyphenyl glycosides, [140] glycosyl 5-hexynoates, [141] and propargyl glycosides [142] have also been devised in the past decade. Furthermore, the development of new activation systems for existing donors propels carbohydrate chemistry forward.…”

Section: Other Glycosyl Donors and Promotersmentioning

confidence: 99%

New Principles for Glycoside‐Bond Formation

2009

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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.

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“…Synthesis of glycosides 27-31 by using nucleophiles 6-8, 25, and 26 and disarmed glycosyl donor 3 in dichloromethane at room temperature. Reactions were performed by using AuCl 3 [25] cosides 27-31, [26] respectively. Reactions were performed by using AuCl 3 [25] cosides 27-31, [26] respectively.…”

Section: Resultsmentioning

confidence: 99%

AuCl₃– and AuCl₃–Phenylacetylene‐Catalyzed Glycosylations by Using Glycosyl Trichloroacetimidates

et al. 2015

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Glycosylations of armed and disarmed trichloroacetimidate‐based glycosyl donors were carried out by using the AuCl3–phenylacetylene relay catalyst system. The effectiveness of this catalytic system was also compared with that of using AuCl3 alone as a catalyst. Glycosylations with these catalysts proceeded efficiently at room temperature within 5–45 min. Excellent diastereoselectivity was obtained for the glycosylation of 2‐O‐acetyl‐protected disarmed glycosyl donors, whereas armed glycosyl trichloroacetimidates gave rise to a mixture of anomeric glycosides. Acid‐sensitive nucleophiles such as Fmoc‐serine tert‐butyl ester or Fmoc‐threonine tert‐butyl ester successfully underwent the glycosylations, albeit in moderate yields, under mild conditions at room temperature.

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Hg(OTf)2-catalyzed glycosylation using alkynoate as the leaving group

Cited by 64 publications

References 43 publications

Chemical O‐Glycosylations: An Overview

Chemical O‐Glycosylations: An Overview

New Principles for Glycoside‐Bond Formation

AuCl₃– and AuCl₃–Phenylacetylene‐Catalyzed Glycosylations by Using Glycosyl Trichloroacetimidates

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Hg(OTf)2-catalyzed glycosylation using alkynoate as the leaving group

Cited by 64 publications

References 43 publications

Chemical O‐Glycosylations: An Overview

Chemical O‐Glycosylations: An Overview

New Principles for Glycoside‐Bond Formation

AuCl3– and AuCl3–Phenylacetylene‐Catalyzed Glycosylations by Using Glycosyl Trichloroacetimidates

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AuCl₃– and AuCl₃–Phenylacetylene‐Catalyzed Glycosylations by Using Glycosyl Trichloroacetimidates