Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 353, Issue 14-15, Pages 2593-2598Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201100228
Keywords
carbohydrates; catalysis; copper(II) triflate; oligosaccharide synthesis; one-pot procedure
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Funding
- Novartis
- EPSRC
- Royal Society
- Engineering and Physical Sciences Research Council [EP/F027222/1] Funding Source: researchfish
- EPSRC [EP/F027222/1] Funding Source: UKRI
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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.
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