An Efficient One-Stage Deprotection/Reduction of 1,2-O-Isopropylidene Furanoses to the Corresponding Tetrahydrofurans
Gregory J. Ewing and Morris J. Robins*
*Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, Email:
G. J. Ewing, M. J. Robins, Org. Lett., 1999, 1, 635-636.
DOI: 10.1021/ol9901117 (free Supporting Information)
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Treatment of 1,2-O-isopropylidenefuranose derivatives with triethylsilane/boron trifluoride etherate provides tetrahydrofurans. The removal of the 1,2-O-isopropylidene group is accompanied by deoxygenation at the anomeric position. This process is compatible with several hydroxyl protecting groups.
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