Einwirkung von Quecksilbersalzen auf Aceto‐halogen‐zucker, IX. Mitteil.: Synthese von Derivaten der β‐1‐l‐Rhamnosido‐6‐
            <i>d</i>
            ‐glykose

Zemplén, Geža; Gerecs, Árpád

doi:10.1002/cber.19340671224

Cited by 27 publications

(3 citation statements)

References 2 publications

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“…201 Zemplen and co-worker employed titanium tetrabromide for the synthesis of glycosyl bromide wherein a solution of titanium tetrabromide in chloroform was added to a solution of tetra-acetylated rhamnose in chloroform to produce acetobromo-α-L-rhamnose in an excellent yield and in crystalline form. 202 This protocol works well for the synthesis of 2-azido-2-deoxy bromides. 203 More recent methods were predominantly focused on the development of milder reaction conditions for the formation of anomeric bromides.…”

Section: Synthesis Of Glycosyl Bromidesmentioning

confidence: 87%

“…In early days, a few other methods such as red phosphorus/bromine or PBr 3 were commonly used for the synthesis of bromides . Zemplen and co-worker employed titanium tetrabromide for the synthesis of glycosyl bromide wherein a solution of titanium tetrabromide in chloroform was added to a solution of tetra-acetylated rhamnose in chloroform to produce acetobromo-α- l -rhamnose in an excellent yield and in crystalline form . This protocol works well for the synthesis of 2-azido-2-deoxy bromides …”

Section: Glycosyl Bromidesmentioning

confidence: 99%

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Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century

2022

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Advances in synthetic carbohydrate chemistry have dramatically improved access to common glycans. However, many novel methods still fail to adequately address challenges associated with chemical glycosylation and glycan synthesis. Since a challenge of glycosylation has remained, scientists have been frequently returning to the traditional glycosyl donors. This review is dedicated to glycosyl halides that have played crucial roles in shaping the field of glycosciences and continue to pave the way toward our understanding of chemical glycosylation.

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Section: Synthesis Of Glycosyl Bromidesmentioning

confidence: 87%

Section: Glycosyl Bromidesmentioning

confidence: 99%

Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century

2022

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“…Treatment of 2-acetyl-1 ,3-dimethylpyrogallol with aluminium chloride in nitrobenzene gave a rearrangement product, acetosyringone (2) [5], which was identified by IR, Mass and 'H NMR spectra, and mixed melting point determination. Condensation of 2 with 2, 3, 4, 6-tetra-Oacetyl-a-D-glucosyl bromide [6] in toluene in the presence of cadmium carbonate [7] gave 3. Treatment of 3 with 5 % Ba(OH)2 gave I which was identified with the naturally occurring glycoside by JR and 'H-NMR spectra, specific rotation, and mixed melting point determination.…”

Section: R=hmentioning

confidence: 99%

Glucoacetosyringone fromRanzania japonica

Ina¹,

Yamauchi²,

Iida³

1983

Planta Med

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Ranzania japonica; Podophyllaceae; 13C NMR; Glucoacetosyringone; Acetosyringone. Glucoacetosyrin gone, a new glycoside, has been isolated from Ranzania japonica and shown to be3,5-dimethoxy-4hydroxyacetophenone 4-O-f3-D-glucopyranoside. Ranzania japonica (Podophyllaceae) is a Japanese plant named Togakushishoma [11. Several antitumour lignans such as podophyllotoxin have been isolated from this family [2]. We have isolated a new glycoside, glucoacetosyrin-* The spectrum was measured with a JNM FX-1 00 spectrometer (25 MHz) in DMSO-12C-d6 with TMS as an internal reference. t Assignments bearing the same superscript may be reversed.

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Besonderheiten der Zucker von herzaktiven Glykosiden

Reichstein

1962

Angewandte Chemie

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Wenn man die Zuckerkomponenten der digitaloiden Lactone (sowie zweier weiterer kleiner Stoffgruppen) mit denjenigen der übrigen natürlichen Glykoside der höheren Pflanzen vergleicht, so ergeben sich auffallende Unterschiede: Nicht digitaloide Glykoside enthalten als Bausteine fast stets einen oder mehrere der acht Zucker D‐Glucose, D‐Glucuronsäure, D‐Xylose, L‐Arabinose, D‐Galactose, D‐Galacturonsäure, L‐Fucose, L‐Rhamnose. Oligosaccharid‐Anteile enthalten fast stets die Hexose „innen”︁, d. h. direkt an das Aglykon gebunden, Pentosen und Methylpentosen „außen”︁. Oligosaccharid‐Anteile mit mehr als zwei Zuckern scheinen oft verzweigt zu sein. In herzaktiven Glykosiden (und zwei verwandten kleinen Stoffgruppen) kommen von den acht Zuckern nur D‐Glucose und L‐Rhamnose häufig vor. Sehr oft werden zahlreiche andere Zucker gefunden, besonders Hexamethylosen. Oligosaccharid‐Anteile enthalten die Hexose (D‐Glucose) immer „außen”︁. Oligosaccharid‐Anteile mit mehr als zwei Zuckern sind, soweit bekannt, immer linear gebaut.

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Einwirkung von Quecksilbersalzen auf Aceto‐halogen‐zucker, IX. Mitteil.: Synthese von Derivaten der β‐1‐l‐Rhamnosido‐6‐ d ‐glykose

Cited by 27 publications

References 2 publications

Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century

Synthesis and Glycosidation of Anomeric Halides: Evolution from Early Studies to Modern Methods of the 21st Century

Glucoacetosyringone fromRanzania japonica

Besonderheiten der Zucker von herzaktiven Glykosiden

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