Über zwei neue Derivate von Trehalose und Mannit und über ein α‐Methylglucosid‐dichlorhydrin

Helferich, Burckhardt; Löwa, Albrecht; Nippe, Waldemar; Riedel, H.J.

doi:10.1002/cber.19230560516

Cited by 14 publications

(10 citation statements)

References 1 publication

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“…The chloroform extract was concentrated to a syrup (1. The infrared spectrum of the compound showed a strong absorption frequency a t 1410 cm-I and a weak one a t 1197 cm-I (cyclic sulphate ester), and the physical constants and analysis indicate that it is identical with the compound isolated by Helferich et al (2).…”

Section: Reaction Of Methyl 46-0-ethylidene-a-d-mannopyranoside 2s-supporting

confidence: 50%

“…The ester (IV) when treated with pyridine gave a crystalline derivative which was shown by analysis to be a tetrachlorotetradeoxy cyclic sulphate ester (2,4). This evidence indicates that the chlorosulphate groups in the original compound (IV) must have been vicinal.…”

Section: Introductionmentioning

confidence: 94%

“…Helferich and co-workers first isolated cyclic sulphate derivatives of methyl a-and methyl P-Dglucopyranoside, of mannitol, and of trehalose (1)(2)(3) and this work has been extended more recently (4,5). The cyclic sulphate ester groups were shown to bridge adjacent hydroxyl groups on Cz and Cs of the glycopyranosides and possibly across Cg and Cd of the D-mannitol derivative (4,5).…”

Section: Introductionmentioning

confidence: 99%

“…Sulphuryl chloride is the only reagent which has been reported to yield cyclic sulphate ester derivatives of carbohydrates (1)(2)(3)(4)(5) and although other methods of forming diol cyclic sulphates are known they do not seem to be applicable in this field (6). Helferich and co-workers first isolated cyclic sulphate derivatives of methyl a-and methyl P-Dglucopyranoside, of mannitol, and of trehalose (1)(2)(3) and this work has been extended more recently (4,5).…”

Section: Introductionmentioning

confidence: 99%

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The Reaction of Chlorosulphate Esters of Sugars With Pyridine

Jennings¹,

Jones²

1963

Can. J. Chem.

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Hexoside and hexitol derivatives with vici~lal chlorosulphate ester groups in different configurations were treated with pyridine. The corresponding cyclic sulphate esters were produced except in the case of the diaxial configuration, which gave a n anyhdro derivative. The axial-equatorial configuration gave in addition a lreto-deoxy compound. The structures of the cyclic sulphate esters and of other reaction products are proposed and their mode of formation is discussed.

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Section: Reaction Of Methyl 46-0-ethylidene-a-d-mannopyranoside 2s-supporting

confidence: 50%

Section: Introductionmentioning

confidence: 94%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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The Reaction of Chlorosulphate Esters of Sugars With Pyridine

Jennings¹,

Jones²

1963

Can. J. Chem.

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“…i\/Iost of the work recorded t o date on the reaction of sulfuryl chloride with pyranose sugars (1-7) has been concerned with those in the xylo-or arabinoconfiguration and has indicated that position G4 is the only secondary hydroxyl group to be converted readily to a chlorodeoxy group, with inversion of configuration. This inversion of configuration probably occurs via intermediate chlorosulfate ester groups (1)(2)(3)(4)(5)(6)(7). Positions Cz and C3 were found to be comparatively unreactive to chlorosubstitution.…”

Section: Introductionmentioning

confidence: 98%

Reactions of Sugar Chlorosulfates: Part V. The Synthesis of Chlorodeoxy Sugars

Jennings¹,

Jones²

1965

Can. J. Chem.

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The reaction of sulfuryl chloride with reducing sugars and their methyl glycopyranosides was shown to produce fully substituted pyranose derivatives containing both chlorodeoxy and chlorosulfate ester groups. I t was demonstrated that the chlorodeoxy groups were formed by llucleophilic displacement ( S N~) by chloride ion of specific reactive chlorosulfate groups in fully chlorosulfated intermediates. The degree of chloro-substitution was shown to be determined by both steric and electronic effects in the individual pyranose derivatives.

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Polyhalogenated Carbohydrates: Synthesis and Applications of Sugar Halides from Fluorine to Iodine

Lessard,

Lainé,

Giguère

2024

Eur J Org Chem

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Polyfluorinated carbohydrates have attracted attention in the last decades. This is due to the interesting properties of such organofluorines. What about the other halogens? Since the discovery of sucralose (a trichlorinated disaccharide) more than 50 years ago, only a handful of chlorinated, brominated, or iodinated carbohydrates have been reported. This review focuses on the synthesis of polyhalogenated carbohydrates, including sugar inter‐halides, but excluding polyfluorinated sugars. An overview of the current state of the art of their potential application is also described.

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Über zwei neue Derivate von Trehalose und Mannit und über ein α‐Methylglucosid‐dichlorhydrin

Cited by 14 publications

References 1 publication

The Reaction of Chlorosulphate Esters of Sugars With Pyridine

The Reaction of Chlorosulphate Esters of Sugars With Pyridine

Reactions of Sugar Chlorosulfates: Part V. The Synthesis of Chlorodeoxy Sugars

Polyhalogenated Carbohydrates: Synthesis and Applications of Sugar Halides from Fluorine to Iodine

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