(2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran

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CAS: 53008-63-2
MF: C35H38O6
MW: 554.67262
Synonyms: (2R,3S,4S,5R,6S)-3,4,5-Tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran

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Hung-wen Liu

University of Texas at Austin
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C. Meier

University of Hamburg
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John Gardiner

The University of Manchester
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Gavin Miller

The University of Manchester
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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