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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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Abstract

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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Key Words

acetonides, tetrahydrofurans, triethylsilane, deoxygenation


ID: J54-Y1999