Scinopharm Taiwan, Ltd.

Chen-Wei Lin

Julian Paul Henschke

Jyh-Hsiung Liao

Ping-Yu Wu

Tsung-Yu Hsiao

Chi-Nung Hsiao

The present application discloses a stereoselective process for the preparation of &#x3b2;-C-arylglucosides that does not require the use of conventional carbohydrate protecting groups. In one embodiment, the stereoselective process comprises the preparation of the compound of formula I: the process comprising: a) contacting 1,6-anhydro-&#x3b2;-D-glucopyranose with a compound of formula II, RRRAl, in a solvent to form a first reaction mixture; b) contacting the first reaction mixture of step a) with a second reaction mixture to form a third reaction mixture, wherein the second reaction mixture is prepared by contacting an organoaluminum compound of formula III, RRAlX, with a compound of formula IV, ArM; and c) contacting the third reaction mixture with a reagent to form the compound of the formula I.

[object Object]

The present invention provides processes (e.g., arylation reaction) for stereoselectively preparing C-arylglucosides that can be useful as synthetic building block or drugs, including SGLT2 inhibitors. A representative process of the present application includes the preparation of the compound of formula IV starting from a compound of the formula II with a metalated aryl compound, as disclosed below: 

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Chen-Wei Lin