Highly Selective β-Mannosylations and β-Rhamnosylations Catalyzed by Bis-thiourea.

Journal of the American Chemical Society
Qiuhan LiEric N Jacobsen

Abstract

We report highly β-selective bis-thioureas-catalyzed 1,2-cis-O-pyranosylations employing easily accessible acetonide-protected donors. A wide variety of alcohol nucleophiles, including complex natural products, glycosides, and amino acids were β-mannosylated and β-rhamnosylated successfully using an operationally simple protocol under mild and neutral conditions. Less nucleophilic acceptors such as phenols were also glycosylated efficiently in excellent yields and with high β-selectivities.

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Citations

Oct 27, 2020·The Journal of Organic Chemistry·Robin A JeanneretM Carmen Galan
Jun 5, 2021·Journal of the American Chemical Society·Gaoyuan ZhaoMing-Yu Ngai
Jun 12, 2021·Journal of the American Chemical Society·Yuntao ZhuPeter H Seeberger
Jul 8, 2021·Organic & Biomolecular Chemistry·Guosheng FangGang Zhao
Aug 14, 2021·Beilstein Journal of Organic Chemistry·Giulio FittolaniMartina Delbianco
Oct 8, 2021·ACS Chemical Biology·Laura L Kiessling, Roger C Diehl
Dec 22, 2021·Organic & Biomolecular Chemistry·Florian Gallier, Leandro Soter de Mariz E Miranda
Dec 1, 2021·Angewandte Chemie·Michael Martin NielsenChristian Marcus Pedersen
Feb 4, 2022·Journal of the American Chemical Society·Wei-Cheng ZhaoZhi-Tao He

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