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Stereoselective synthesis of β-rhamnopyranosides via gold(i)-catalyzed glycosylation with 2-alkynyl-4-nitro-benzoate donors†
Yugen Zhu,Zhengnan Shen,Wei Li,Biao Yu
Organic & Biomolecular Chemistry Pub Date : 12/15/2015 00:00:00 , DOI:10.1039/C5OB02551F
Abstract

Stereoselective β-rhamnopyranosylation remains a challenge, due to the unfavorable anomeric effect and steric hindrance of the C2-substituent; herein, this challenge is addressed with a gold(I)-catalyzed SN2-like glycosylation protocol employing α-rhamnopyranosyl 2-alkynyl-4-nitro-benzoates as donors.

Graphical abstract: Stereoselective synthesis of β-rhamnopyranosides via gold(i)-catalyzed glycosylation with 2-alkynyl-4-nitro-benzoate donors
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