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Methyl (2'S,3'S)-3,4-O-(2',3'-dimethoxy-butane-2',3'-di-yl)-?-l-rhamnopyran-oside: a glycosyl acceptor.

ABSTRACT: The title compound, C(13)H(24)O(7), is the product of the ketalization of methyl l-(+)-rhamnopyran-oside with 2,3-butane-dione. It crystallizes with two mol-ecules in the asymmetric unit, which are connected by O-H?O hydrogen bonds. The C-3,4 diequatorial hydroxy groups of the methyl l-(+)-rhamnopyran-oside were protected, leaving the C-2 hydroxy group free. The l-(+)-rhamnopyran-oside and 2',3'-dimethoxy-butane-2',3'-diyl rings adopt chair conformations and all meth-oxy groups are in axial positions. The absolute configuration was assumed from the synthesis.

SUBMITTER: Tsai YF 

PROVIDER: S-EPMC2961327 | biostudies-literature | 2008 Apr

REPOSITORIES: biostudies-literature

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Methyl (2'S,3'S)-3,4-O-(2',3'-dimethoxy-butane-2',3'-di-yl)-α-l-rhamnopyran-oside: a glycosyl acceptor.

Tsai Yow-Fu YF   Yang Jen-Ta JT   Chen Jhy-Der JD   Lin Chia-Her CH  

Acta crystallographica. Section E, Structure reports online 20080423 Pt 5

The title compound, C(13)H(24)O(7), is the product of the ketalization of methyl l-(+)-rhamnopyran-oside with 2,3-butane-dione. It crystallizes with two mol-ecules in the asymmetric unit, which are connected by O-H⋯O hydrogen bonds. The C-3,4 diequatorial hydroxy groups of the methyl l-(+)-rhamnopyran-oside were protected, leaving the C-2 hydroxy group free. The l-(+)-rhamnopyran-oside and 2',3'-dimethoxy-butane-2',3'-diyl rings adopt chair conformations and all meth-oxy groups are in axial posi  ...[more]

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