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.
Articolo in rivista - Articolo scientifico
Scientifica
Protecting groups, carbohydrates
English
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.
Peri, F; Cipolla, L; LA FERLA, B; Nicotra, F
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/10281/16625
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