Nissan Chemical Industries Limited

Akiko Yamazaki

Yusuke Iriyama

Yoshikazu Ootsuka

Tomohiro Akeboshi

The invention provides a process for producing a &#x3b2;-glycoside compound represented by formula (3), characterized in that the process includes causing to react a cyclic alkene compound represented by formula (1) or (2) with a nucleophile in the presence of a transition metal catalyst. 

Process for preparation of &#x3b2;-glycoside compounds

An acylating agent and a hydrolase are caused to act on a hydroxypyranone represented by formula (I) in a water-containing organic solvent, to thereby produce an acyloxypyranone compound represented by formula (II) (wherein Rrepresents an acyl group). Then, an acetylene organic metal compound represented by formula (III) (wherein Rrepresents a hydrogen atom or a tri-substituted silyl group, and M represents an alkali metal atom, aluminum, or a magnesium monohalide) and a coordinating additive are caused to act on the acyloxypyranone compound represented by formula (II), to thereby produce an alkyne compound represented by formula (IV). The alkyne compound represented by formula (IV) is hydrolyzed with acid, to thereby produce a dihydrofuran compound represented by formula (V). 

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Funabashi, Japan

Akiko Yamazaki