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-α-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, F., Cipolla, L., LA FERLA, B., Nicotra, F. (2000). Regioselection and orthogonality of the 1-phenyl-3-butenyl (PBU) protecting group in glucopyranosides. CARBOHYDRATE LETTERS, 4(1), 21-27.
Regioselection and orthogonality of the 1-phenyl-3-butenyl (PBU) protecting group in glucopyranosides
PERI, FRANCESCO;CIPOLLA, LAURA FRANCESCA;LA FERLA, BARBARA;NICOTRA, FRANCESCO
2000
Abstract
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-α-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.
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