Collect. Czech. Chem. Commun.
2007, 72, 411-416
https://doi.org/10.1135/cccc20070411
An Easy Regio- and Stereoselective Synthesis of a Versatile Trisaccharide Precursor for Synthetic Carbohydrate Based Vaccines
Juan A. Mesaa,*, Juan E. Tacorontea, Ernesto Garcíab and Jorge Leyvac
a Centro de Ingeniería e Investigaciones Químicas, Vía Blanca s/n entre Infanta y Palatino, Cerro, Ciudad de La Habana, Cuba
b Centro de Estudio de Antígenos Sintéticos, Facultad de Química, Universidad de La Habana, Cuba
c Empresa Farmacéutica "Mario Munoz", Hacendado 1, Habana Vieja, Ciudad de La Habana, Cuba
Abstract
The trisaccharide allyl 2-deoxy-2-phthalimido-6-O-[4-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-β-D-glucopyranosyl]-β-D-glucopyranoside (3) was prepared directly from acceptor allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (1) and 4-O-(2,3,4,6- tetra-O-benzoyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzoyl-α-D-glucopyranosyl trichloroacetimidate (2c) using regio- and stereoselective synthesis in dichloromethane with trimethylsilyl triflate as a promoter.
Keywords: Trisaccharides; Oligosaccharides; Carbohydrates; Glycosidation; Regioselective synthesis; Stereoselective synthesis.
References: 13 live references.
