Advanced Synthesis and Catalysis p. 2593 - 2598 (2011)
Update date:2022-08-04
Topics:
Tran, Anh-Tuan
Jones, Rachel A.
Pastor, Julien
Boisson, Julien
Smith, Nichola
Galan, M. Carmen
The development of general and expedient methodologies for the preparation of orthogonally protected glycoside building blocks is essential for the efficient synthesis of complex oligosaccharides. Herein, we describe a new approach that uses copper(II) triflate as a versatile catalyst for the one-pot preparation of orthogonal protected thio- and O-glycosides from the corresponding unprotected counterparts. The conditions are mild, easy to handle and applicable to two and three one-pot tandem transformations, which include arylidene acetalation, esterification, regioselective reductive acetal ring opening, glycosylation and silylation processes. Copyright
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