B(C(6)F(5))(3)-Catalyzed Stereoselective 1,2-cis Arabinofuranosylation with a Conformationally Constrained Donor

B(C(6)F(5))(3)催化的构象受限供体立体选择性1,2-顺式阿拉伯呋喃糖基化反应

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Abstract

Compared with stereoselective glycosylation methods mainly addressed on the preparation of pyranose glycosides, the furanosylation has been more limited, especially for the 1,2-cis arabinofuranosylation. Herein, we report a novel stereoselective 1,2-cis-arabinofuranosylation strategy using a conformationally restricted 3,5-O-xylylene-protected arabinofuranosyl donor on activation with B(C(6)F(5))(3) for desired targets in moderate to excellent yields and β-stereoselectivity. The effectiveness of the 1,2-cis-arabinofuranosylation strategy was demonstrated successfully with various acceptors, including carbohydrate alcohols.

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