3-Ammonio-l,6-anhydro-3-deoxy-β-<scp>D</scp>-glucopyranose chloride monohydrate

Małuszyńska, H.; Takagi, S.

doi:10.1107/s0567740877007079

Cited by 15 publications

(1 citation statement)

References 6 publications

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“…(16), and its hydrochloride and other cationic derivatives exist predominantly in the latter conformation. Both compounds are present in the chair conformation in the solid state (36,37). One explanation considered for the unusual conformation of 18 was that the NH2 group was larger than an OH group (16).…”

Section: Resultsmentioning

confidence: 99%

Syntheses of 3-deoxy-3-substituted-D-glucose derivatives. Part I. Improvements in preparation of and nucleophilic additions to 1,6:2,3-dianhydro-4-O-benzyl-β-D-allopyranose

Grindley¹,

Reimer²,

Kralovec³

et al. 1987

Can. J. Chem.

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The yield of the five-step preparation of 1,6:2,3-dianhydro-4-O-benzyl-β-D-allopyranose from 1,6-anhydro-β-D-glucopyranose has been raised to 33% from 12% by modifying conditions or methods for four of the steps. It has been demonstrated that nucleophilic addition to the former compound provides a general route to 1,6-anhydro-3-deoxy-3-substituted-β-D-glucopyranose derivatives, although reactions with large nucleophiles proceed either slowly or not at all. A number of nucleophiles, including chloride, fluoride, cyanide, alkylsulfide, and dimethylamine, gave this type of product in good yield (73–87%). The conditions used to introduce a chloro group, a catalytic amount of tetraethylammonium chloride in 1,1,2,2-tetrachloroethane at reflux, had not previously been used for carbohydrate epoxides. The methyl substituted product was obtained in highest yield with dimethyl magnesium. By-products from this reaction included the products of a Witting rearrangement and of an elimination. All addition products were present in the 1C4 conformation.

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Section: Resultsmentioning

confidence: 99%

Syntheses of 3-deoxy-3-substituted-D-glucose derivatives. Part I. Improvements in preparation of and nucleophilic additions to 1,6:2,3-dianhydro-4-O-benzyl-β-D-allopyranose

Grindley¹,

Reimer²,

Kralovec³

et al. 1987

Can. J. Chem.

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Structural studies of crystalline oligosaccharides VI: Crystal structure and conformation of benzyl‐4,6‐O‐benzylidene‐3‐O‐benzoyl‐β‐D‐galactoside

Shen

Srikrishnan²

2006

Cryst. Res. Technol.

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Monsaccharides are the building blocks of polysaccharides and hence are the simplest sugar molecules to study the conformation and molecular structures of sugars. Benzyl-4,6-O-benzylidene-3-O-benzoyl-β-Dgalactoside is a key intermediate in the synthesis of polysaccharides. Crystal structural investigation of the title compound was undertaken to establish their chemical structure as well as to study their solid state conformation. Crystals of the title compound, obtained from water/methanol, are orthorhombic, space group P2 1 2 1 2 1 , with cell dimensions a=11.290 (4), b=9.941 (1) , 2886 reflections were collected on a CAD-4 diffractometer. The structure was solved by direct methods and refined to a final reliability index of 4.7%. The galactoside sugar has the chair conformation with C2' and C5' deviating from the mean plane of the other atoms of the sugar. The 4,6-Obenzylidene ring also has a chair conformation with the benzoyl group proximal to O6'. The crystal structure is stabilized by O-H…O hydrogen bonds involving O2' as donor and three C-H…O hydrogen bond interactions.

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Structure and Conformation of Carbohydrates

Grindley¹

2008

Glycoscience

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3-Ammonio-l,6-anhydro-3-deoxy-β-D-glucopyranose chloride monohydrate

Cited by 15 publications

References 6 publications

Syntheses of 3-deoxy-3-substituted-D-glucose derivatives. Part I. Improvements in preparation of and nucleophilic additions to 1,6:2,3-dianhydro-4-O-benzyl-β-D-allopyranose

Syntheses of 3-deoxy-3-substituted-D-glucose derivatives. Part I. Improvements in preparation of and nucleophilic additions to 1,6:2,3-dianhydro-4-O-benzyl-β-D-allopyranose

Structural studies of crystalline oligosaccharides VI: Crystal structure and conformation of benzyl‐4,6‐O‐benzylidene‐3‐O‐benzoyl‐β‐D‐galactoside

Structure and Conformation of Carbohydrates

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