Synthesis and role of glycosylthio heterocycles in carbohydrate chemistry

Ashry, El Sayed H. El; Awad, Laila F.; Atta, Abdu Mohammed Ali

doi:10.1016/j.tet.2005.11.045

Cited by 84 publications

(33 citation statements)

References 101 publications

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“…Very importantly, no side products of the acceptor self-condensation were detected. The advantage of the oligosaccharide synthesis through selective activation is that all formed disaccharides 70,71,73,74,76,78,80,82,84, and 86 could be subsequently activated for the second-step glycosidation. Apparently, the second-step activation should be feasible in the presence of NIS/TfOH or other activators suitable for the activation of S-alkyl/aryl or O-pentenyl moieties.…”

Section: Resultsmentioning

confidence: 99%

“…[78,79] The roles and applications of this class of compounds have been recently reviewed. [69,80] Experimental Section General: Column chromatography was performed on silica gel 60 (EM Science, 70-230 mesh), reactions were monitored by TLC on Kieselgel 60 F 254 (EM Science). The compounds were detected by examination under UV light and by charring with 10 % sulfuric acid in methanol.…”

Section: Resultsmentioning

confidence: 99%

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S‐Thiazolinyl (STaz) Glycosides as Versatile Building Blocks for Convergent Selective, Chemoselective, and Orthogonal Oligosaccharide Synthesis

Pornsuriyasak

Demchenko

2006

Chemistry A European J

103

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In the aim of developing new procedures for efficient oligosaccharide assembly, a range of S-thiazolinyl (STaz) glycosides have been synthesized. These novel derivatives were evaluated against a variety of reaction conditions and were shown to be capable of being chemoselectively activated in the armed-disarmed fashion. Moreover, the S-thiazolinyl moiety exhibited a remarkable propensity for selective activation over other common leaving groups. Conversely, a variety of leaving groups could be selectively activated over the STaz moiety, which, in turn, allowed STaz/S-ethyl and STaz/S-phenyl orthogonal approaches. To demonstrate versatility of novel STaz derivatives, a number of oligosaccharide targets have been synthesized in a convergent selective, orthogonal, and chemoselective fashion.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

S‐Thiazolinyl (STaz) Glycosides as Versatile Building Blocks for Convergent Selective, Chemoselective, and Orthogonal Oligosaccharide Synthesis

Pornsuriyasak

Demchenko

2006

Chemistry A European J

103

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“…[87] Two classical routes to glycosyl thioimidates involve the Lewis acid promoted displacement of anomeric acetoxy groups with thiol aglycones or the displacement of anomeric halogen substituents with thiolate anions. [88] Both procedures are frequently used and high yielding.…”

Section: Glycosyl Thioimidatesmentioning

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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“…The thioglycosyl heterocycles [30][31][32][33] and the acyclic nucleoside analogs with modified glycon part and the heterocyclic base have stimulated extensive research as V C 2011 HeteroCorporation January 2012 93 biological inhibitors [34][35][36]. In view of the above findings and our interest in the attachment of sugar moieties to newly synthesized heterocycles [37][38][39], we report in the present work the synthesis of new substituted [(pyrazol-4-yl)methylene]hydrazono-2,3-dihydrothiazole derivatives and their substituted sugar derivatives.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial activity of substituted [(pyrazol‐4‐yl)methylene]hydrazono‐2,3‐dihydrothiazoles and their sugar derivatives

Abdel‐Rahman¹,

El‐Sayed²,

Zaki³

et al. 2011

Journal of Heterocyclic Chem

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A number of new [(pyrazol-4-yl)methylene]hydrazono-2,3-dihydrothiazole derivatives, their sugar hydrazones and N-glycosides were synthesized. Furthermore, N-substituted oxygenated alkyl and hydroxyl derivatives and 1,3,4,-oxadiazoline acyclic nucleoside analogs were prepared. The newly synthesized compounds were tested for their antimicrobial activities and showed moderate to high inhibition activities.

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Synthesis and role of glycosylthio heterocycles in carbohydrate chemistry

Cited by 84 publications

References 101 publications

S‐Thiazolinyl (STaz) Glycosides as Versatile Building Blocks for Convergent Selective, Chemoselective, and Orthogonal Oligosaccharide Synthesis

S‐Thiazolinyl (STaz) Glycosides as Versatile Building Blocks for Convergent Selective, Chemoselective, and Orthogonal Oligosaccharide Synthesis

New Principles for Glycoside‐Bond Formation

Synthesis and antimicrobial activity of substituted [(pyrazol‐4‐yl)methylene]hydrazono‐2,3‐dihydrothiazoles and their sugar derivatives

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