Affiliation:
1. Department of Applied Chemistry Faculty of Science and Technology Keio University 3-14-1 Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan
2. Department of Chemistry Faculty of Science and Technology Keio University 3-14-1 Hiyoshi, Kohoku-ku Yokohama 223-8522 Japan
Abstract
AbstractHere reports an photoinduced glycosylation of trichloroacetimidate donors and several alcohols using 3,11‐dimethoxydinaphthothiophene as an organo Lewis photoacid catalyst upon long‐wavelength UV‐LED light (385 nm) irradiation. The reaction proceeded under mild reaction conditions smoothly to give the corresponding glycosides in good to high yields. In addition, the present glycosylation method was applicable to a wide range of trichloroacetimidate donors and acceptors. Furthermore, the dinaphthothiophene catalyst could be recovered and reused without any loss of efficiency. Moreover, this glycosylation method was applied successfully to the total synthesis of a biologically active natural product, cholesteryl 6‐O‐myristoyl‐α‐glucoside.
Subject
Organic Chemistry,Physical and Theoretical Chemistry
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