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

Qian Xiao; Sixian Fang; Jiaming Ao; Xiaoya Zhao; Cai Huang; Yuhua Liu; Yichu Nie; Akihiro Ishiwata; Katsunori Tanaka; Wenbin Deng; Feiqing Ding

doi:10.1021/acsomega.3c09761

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

ACS Omega. 2024 Mar 4;9(10):11969-11975. doi: 10.1021/acsomega.3c09761. eCollection 2024 Mar 12.

Authors

Qian Xiao¹, Sixian Fang¹, Jiaming Ao¹, Xiaoya Zhao¹, Cai Huang¹, Yuhua Liu², Yichu Nie³, Akihiro Ishiwata⁴, Katsunori Tanaka^{4

5}, Wenbin Deng¹, Feiqing Ding¹

Affiliations

¹ School of Pharmaceutical Sciences (Shenzhen), Shenzhen Campus of Sun Yat-sen University, Shenzhen 518107, China.
² School of Physics and Electronic Engineering, Guangzhou University, Guangzhou 510006, China.
³ Translational Medicine Research Institute, First People's Hospital of Foshan, Foshan 528000, China.
⁴ RIKEN Cluster for Pioneering Research, Wako, Saitama 3510198, Japan.
⁵ Department of Chemical Science and Engineering, Tokyo Institute of Technology, Tokyo 152-8552, Japan.

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(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.