((2R,3R,4S,5S,6R)-6-Acetoxy-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)methyl acetate

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CAS: 65556-30-1
MF: C31H34O8
MW: 534.59686
Synonyms: ((2R,3R,4S,5S,6R)-6-Acetoxy-3,4,5-tris(benzyloxy)tetrahydro-2H-pyran-2-yl)methyl acetate

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Stefan Lutz

Emory University
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Frank E. McDonald

Emory University
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Paul V. Murphy

National University of Ireland Galway
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Co-reporter: Dilip V. Jarikote, Ciaran O’Reilly, Paul V. Murphy
pp: 6776-6778
Publication Date(Web):22 December 2010
DOI: 10.1016/j.tetlet.2010.10.113
A significant rate enhancement was observed in the preparation of allyl and allenyl-C-glycosides from glycosyl acetate or methyl O-glycoside precursors when ultrasound irradiation was employed as an energy source. The C-glycosides were obtained in 77–96% yields in <20 min using TMSOTf as promoter. These results show that sonication provides rapid and efficient access to useful C-glycoside-based building blocks.Image for unlabelled figure