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4-Methoxy-phenyl 2,3,4,6-tetra-O-acetyl-1-thio-?-d-mannopyran-oside.

ABSTRACT: The title compound, C(21)H(26)O(10)S, was synthesized in a single step from mannose penta-acetate. The mol-ecular structure confirms the ? configuration of the anomeric thioaryl substituent. Spectroscopic and melting-point data obtained for the title compound are in disagreement with those previously reported, indicating the previously reported synthesis [Durette & Shen (1980 ?). Carbohydr. Res. 81, 261-274] to be erroneous. The crystal structure is stabilized by weak inter-molecular C-H?O hydrogen bonds.

SUBMITTER: Drouin L 

PROVIDER: S-EPMC2962034 | biostudies-literature | 2008 Jul

REPOSITORIES: biostudies-literature

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4-Methoxy-phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-d-mannopyran-oside.

Drouin Ludovic L   Cowley Andrew R AR   Fairbanks Antony J AJ   Thompson Amber L AL  

Acta crystallographica. Section E, Structure reports online 20080705 Pt 8

The title compound, C(21)H(26)O(10)S, was synthesized in a single step from mannose penta-acetate. The mol-ecular structure confirms the α configuration of the anomeric thioaryl substituent. Spectroscopic and melting-point data obtained for the title compound are in disagreement with those previously reported, indicating the previously reported synthesis [Durette & Shen (1980 ▶). Carbohydr. Res. 81, 261-274] to be erroneous. The crystal structure is stabilized by weak inter-molecular C-H⋯O hydro  ...[more]

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