Ueber die Glucoside der Alkohole

Fischer, Emil

doi:10.1002/cber.18930260327

Cited by 325 publications

(90 citation statements)

References 3 publications

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“…[91] Interestingly, recent mechanistic studies indicated that both MeOTf and AgOTf activate this type of donor at the anomeric sulfur atom. [92] S-Thiazolinyl (STaz) glycosides, such as 21, are also efficient glycosyl donors upon activation with AgOTf, Cu-(OTf) 2 , MeOTf, NIS/TfOH, or other promoter systems. [93] Their reaction with a variety of acceptors provided the corresponding glycosides in high yields (Scheme 3 c).…”

Section: Glycosyl Thioimidatesmentioning

confidence: 99%

“…This awkward situation may be improved at least in some instances by the impressive one-pot procedure developed initially by Hung and co-workers and later by Beau and co-workers for the regioselective protection of carbohydrates. [209] Sugar building blocks with different protection patterns were produced rapidly by this procedure, in which a single Lewis acid, TMSOTf or Cu(OTf) 2 , was used to catalyze a sequence of reactions in a single reaction vessel. The desired building blocks were obtained by tuning the reaction conScheme 17.…”

Section: One-pot Regioselective Protection and "Unichemo" Protectionmentioning

confidence: 99%

“…Thus, the stereoselective formation of O-glycosidic bonds is the key process in most glycoside syntheses. Since the first glycoside syntheses by Michael [1] and Fischer, [2] followed by the seminal studies of Koenigs and Knorr, [3] a very large number of glycosidation methods have been developed. In this Review, advances in the formation of O-glycoside bonds are examined, with emphasis placed on developments in the last ten years.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Glycosyl Thioimidatesmentioning

confidence: 99%

Section: One-pot Regioselective Protection and "Unichemo" Protectionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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New Principles for Glycoside‐Bond Formation

2009

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“…[32,33] Subsequent acetylation allowed the isolation of anomerically pure glycosides 3, 4, 7, and 8 in good yields by column chromatography (Scheme 2). Thus, a fairly large repertoire of monomeric building blocks can be obtained in only two steps (see the Supporting Information for experimental procedures).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of Benzaldehyde‐Functionalized Glycans: A Novel Approach Towards Glyco‐SAMs as a Tool for Surface Plasmon Resonance Studies

Kopitzki

Jensen

Thiem

2010

Chemistry A European J

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In recent years the interest in tools for investigating carbohydrate-protein (CPI) and carbohydrate-carbohydrate interactions (CCI) has increased significantly. For the investigation of CPI and CCI, several techniques employing different linking methods are available. Surface plasmon resonance (SPR) imaging is a most appropriate tool for analyzing the formation of self-assembled monolayers (SAM) of carbohydrate derivatives, which can mimic the glycocalyx. In contrast to the SPR imaging methods used previously to analyze CPI and CCI, the novel approach reported herein allows a facile and rapid synthesis of linker spacers and carbohydrate derivatives and enhances the binding event by controlling the amount and orientation of ligand. For immobilization on biorepulsive amino-functionalized SPR chips by reductive amination, diverse aldehyde-functionalized glycan structures (glucose, galactose, mannose, glucosamine, cellobiose, lactose, and lactosamine) have been synthesized in several facile steps that include olefin metathesis. Effective immobilization and the first binding studies are presented for the lectin concanavalin A.

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“…1 Membros importantes desta família são alquil poliglicosídeos (APGs), os quais têm sido relatados por aproximadamente 120 anos. 2 Alquil poliglicosídeos são considerados surfactantes verdes e bons substitutos dos biosurfactantes que são eficazes para acelerar e melhorar a qualidade da compostagem, mas que são caros e tem uso proibido em adubos microbianos. 3 Alquil poliglicosídeos também têm atraído interesse na suplementação dietética de animais.…”

Section: Introductionunclassified

Synthesis and Characterization of Alkylphenyl Polyglycosidic Surfactants From Amylose and Alkyl Phenols Extracted From Natural CNSL

et al. 2016

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Keywords: synthesis; characterization; alkylphenyl polyglycosidic surfactants; amylose; natural CNSL. INTRODUÇÃOSurfactantes derivados de carboidratos e óleos vegetais são de interesse especial por causa de sua produção a partir de recursos renováveis e suas propriedades ecológicas favoráveis (eles são, por exemplo, biodegradáveis). Estas propriedades os tornam interessante como substitutos de outros agentes tensoativos que são potencialmente prejudiciais à saúde e ao ambiente.1 Membros importantes desta família são alquil poliglicosídeos (APGs), os quais têm sido relatados por aproximadamente 120 anos.2 Alquil poliglicosídeos são considerados surfactantes verdes e bons substitutos dos biosurfactantes que são eficazes para acelerar e melhorar a qualidade da compostagem, mas que são caros e tem uso proibido em adubos microbianos.3 Alquil poliglicosídeos também têm atraído interesse na suplementação dietética de animais. 4 Os surfactantes aniônicos como o lauril sulfato de sódio e o dodecil sulfato de sódio são extensivamente utilizados em cosméticos, embora sejam irritantes para a pele. 5,6 Dessa forma, há a necessidade de novos surfactantes substitutos que não sejam tão agressivos e os alquil poliglicosídeos, surfactantes não-iônicos, apresentam-se como bons candidatos.7 A síntese inicial de alquil poliglicosídeos era e ainda é realizada por dois tipos de matéria prima: carboidratos e álcoois graxos derivados do petróleo. 8 No entanto, novos materiais têm substituído os alcoóis graxos derivados do petróleo por óleos vegetais. 9Neste trabalho optou-se pela utilização de materiais única e exclusivamente de origem vegetal. Os carboidratos utilizados foram extraídos do amido da batata inglesa e o óleo utilizado foi o líquido da casca da castanha do caju (LCC). A amilose foi escolhida como carboidrato para a síntese dos surfactantes, pois ela é um homopolissacarídeo linear do amido. Ela é vantajosa com relação aos heteropolissacarídeos, pois apresenta apenas como único monômero a glicose. O LCC foi escolhido por ser rico em meta alquil fenóis que podem ser utilizados como porção hidrofóbica dos surfactantes. O LCC e seus constituintes são empregados há sete décadas em pesquisas relacionadas à transformação destes materiais em molé-culas de alto valor agregado. [10][11][12][13][14][15][16][17] Esses produtos apresentam várias propriedades importantes do ponto de vista industrial, ambiental, farmacológico ou biológico, tais como: molhabilidade, atoxicidade, baixo valor de cmc, propriedades emulsificantes, boas propriedades dermatológicas, biocompatibilidade, biodegradabilidade, boas propriedades carreadoras e solubilizadoras de drogas 18 e são sintetizados por uma rota sintética verde. 19Os meta alquil fenóis do LCC utilizados neste trabalho foram: o ácido anacárdico, o cardanol e o cardol. Na literatura já existem trabalhos com surfactantes alquil poliglicosídicos derivados do cardanol, 20 no entanto, nenhum trabalho com o ácido anacárdico ou o cardol.

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Ueber die Glucoside der Alkohole

Cited by 325 publications

References 3 publications

New Principles for Glycoside‐Bond Formation

New Principles for Glycoside‐Bond Formation

Synthesis of Benzaldehyde‐Functionalized Glycans: A Novel Approach Towards Glyco‐SAMs as a Tool for Surface Plasmon Resonance Studies

Synthesis and Characterization of Alkylphenyl Polyglycosidic Surfactants From Amylose and Alkyl Phenols Extracted From Natural CNSL

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