An Easy Regio- and Stereoselective Synthesis of a Versatile Trisaccharide Precursor for Synthetic Carbohydrate Based Vaccines
- 1 January 2007
- journal article
- Published by Institute of Organic Chemistry & Biochemistry in Collection of Czechoslovak Chemical Communications
- Vol. 72 (3) , 411-416
- https://doi.org/10.1135/cccc20070411
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
This publication has 11 references indexed in Scilit:
- Phase I Clinical Evaluation of a Synthetic Oligosaccharide-Protein Conjugate Vaccine against Haemophilus influenzae Type b in Human Adult VolunteersClinical and Vaccine Immunology, 2006
- A study of polymer-supported bases for the solution phase synthesis of glycosyl trichloroacetimidatesTetrahedron Letters, 2005
- A Synthetic Conjugate Polysaccharide Vaccine Against Haemophilus influenzae Type bScience, 2004
- Synthesis of Structural Elements of the Capsular Polysaccharide ofStreptococcus PneumoniaeType 14Journal of Carbohydrate Chemistry, 1994
- Total synthesis of X hapten, III3 Fucα-nLc4 CerCarbohydrate Research, 1987
- New Methods for the Synthesis of Glycosides and Oligosaccharides—Are There Alternatives to the Koenigs‐Knorr Method? [New Synthetic Methods (56)]Angewandte Chemie International Edition in English, 1986
- Acute respiratory infections in children under five years. Control project in Bagamoyo District, TanzaniaTransactions of the Royal Society of Tropical Medicine and Hygiene, 1986
- Glycosylimidate, 12 Direkte Synthese von O‐α‐ und O‐β‐Glycosyl‐imidatenEuropean Journal of Organic Chemistry, 1984
- Application of phase sensitive two-dimensional correlated spectroscopy (COSY) for measurements of 1H-1H spin-spin coupling constants in proteinsBiochemical and Biophysical Research Communications, 1983
- Coupure sélective par l'hydrazine des groupements acétyles anomères de résidus glycosyles acétylésCarbohydrate Research, 1975