Regioselection and orthogonality of the 1-phenyl-3-butenyl (PBU) protecting group in glucopyranosides.
The 1-phenyl-3-butenyl (PBU) protecting group was alternatively introduced in position 4 or 6 by regioselective opening of methyl 2,3-di-O-benzyl-4,6-O-benzylidene-alpha-D-glucopyranose with allyltrimethylsilane in the presence of the Lewis acid promoters TMSOTf or AlCl3. The PBU group was selectively removed, in presence of t-butyldimethylsilyl, trityl or acetyl protecting groups, with acids (TFA) or using Pd(CH3CN)2Cl2.
Peri
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Department of Biotechnology and Biosciences, University of Milano-Bicocca, Italy. francesco.nicotra@unimib.it
Cipolla
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Nicotra
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