158198-56-2Relevant academic research and scientific papers
Studies of Catalyst-Controlled Regioselective Acetalization and Its Application to Single-Pot Synthesis of Differentially Protected Saccharides
Wang, Sibin,Zhelavskyi, Oleksii,Lee, Jeonghyo,Argüelles, Alonso J.,Khomutnyk, Yaroslav Ya.,Mensah, Enoch,Guo, Hao,Hourani, Rami,Zimmerman, Paul M.,Nagorny, Pavel
, p. 18592 - 18604 (2021/11/16)
This article describes studies on the regioselective acetal protection of monosaccharide-based diols using chiral phosphoric acids (CPAs) and their immobilized polymeric variants, (R)-Ad-TRIP-PS and (S)-SPINOL-PS, as the catalysts. These catalyst-controll
Iron(iii) chloride-tandem catalysis for a one-pot regioselective protection of glycopyranosides
Bourdreux, Yann,Lemetais, Aurelie,Urban, Dominique,Beau, Jean-Marie
, p. 2146 - 2148 (2011/04/21)
Tandem catalysis by using iron(iii) chloride hexahydrate leads to carbohydrate building blocks displaying an orthogonal protecting group pattern as illustrated by the regioselective protection of trehalose and maltose disaccharides.
Tandem catalysis for a one-pot regioselective protection of carbohydrates: The example of glucose
Francais, Antoine,Urban, Dominique,Beau, Jean-Marie
, p. 8662 - 8665 (2008/09/18)
(Chemical Equation Presented) Fine-tuning the conditions for a tandem reaction using a single catalyst in a single reaction vessel leads to carbohydrate building blocks displaying different patterns of protecting groups (see picture). This process greatly simplifies the access to oligomers, as illustrated by the rapid assembly of a trisaccharide.
Capsular polysaccharide of Streptococcus pneumoniae type 19F: Synthesis of the repeating unit
Bousquet, Ennio,Khitri, Malika,Lay, Luigi,Nicotra, Francesco,Panza, Luigi,Russo, Giovanni
, p. 171 - 181 (2007/10/03)
A new and more versatile synthesis of β-d-ManpNAc-(1→4)-α-d-Glcp-(1→2)-α-l-Rhap, the trisaccharide repeating unit of the Streptococcus pneumoniae type 19F capsular polysaccharide, is described. The present approach allows a simple access to different fragments containing the trisaccharide and the conjugation of the product(s) to a protein through the selective manipulation of the anomeric position at the reducing end and of the HO-4 function at the nonreducing end. The synthetic scheme shows an efficient application of the sulfoxide method for the stereoselective and high yielding formation of the glycosidic linkages. Copyright (C) 1998 Elsevier Science Ltd. A new and more versatile synthesis of β-D-ManpNAc-(1→4)-α-D-Glcp-(1→2)-α-L-Rhap, the trisaccharide repeating unit of the Streptococcus pneumoniae type 19F capsular polysaccharide, is described. The present approach allows a simple access to different fragments containing the trisaccharide and the conjugation of the product(s) to a protein through the selective manipulation of the anomeric position at the reducing end and of the HO-4 function at the nonreducing end. The synthetic scheme shows an efficient application of the sulfoxide method for the stereoselective and high yielding formation of the glycosidic linkages.
