B(C6F5)3‑Catalyzed Stereoselective 1,2-cis Arabinofuranosylation with a Conformationally Constrained Donor

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 conform...

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Published inACS omega Vol. 9; no. 10; pp. 11969 - 11975
Main Authors Xiao, Qian, Fang, Sixian, Ao, Jiaming, Zhao, Xiaoya, Huang, Cai, Liu, Yuhua, Nie, Yichu, Ishiwata, Akihiro, Tanaka, Katsunori, Deng, Wenbin, Ding, Feiqing
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 12.03.2024
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Summary: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(C6F5)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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ISSN:2470-1343
2470-1343
DOI:10.1021/acsomega.3c09761