Regioselection and orthogonality of the 1-phenyl-3-butenyl (PBU) protecting group in glucopyranosides

F Peri; L Cipolla; F Nicotra

Regioselection and orthogonality of the 1-phenyl-3-butenyl (PBU) protecting group in glucopyranosides

Carbohydr Lett. 2000;4(1):21-7.

Authors

F Peri¹, L Cipolla, F Nicotra

Affiliation

¹ Department of Biotechnology and Biosciences, University of Milano-Bicocca, Italy. francesco.nicotra@unimib.it

PMID: 11469334

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-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.