| Id |
Subject |
Object |
Predicate |
Lexical cue |
| T1 |
0-185 |
Sentence |
denotes |
Nickel-catalyzed stereoselective glycosylation with C(2)-N-substituted benzylidene D-glucosamine and galactosamine trichloroacetimidates for the formation of 1,2-cis-2-amino glycosides. |
| T2 |
186-287 |
Sentence |
denotes |
Applications to the synthesis of heparin disaccharides, GPI anchor pseudodisaccharides, and α-GalNAc. |
| T3 |
288-422 |
Sentence |
denotes |
The 1,2-cis-2-amino glycosides are key components found within a variety of biologically important oligosaccharides and glycopeptides. |
| T4 |
423-652 |
Sentence |
denotes |
Although there are remarkable advances in the synthesis of 1,2-cis-2-amino glycosides, disadvantages of the current state-of-the-art methods include limited substrate scope, low yields, long reaction times, and anomeric mixtures. |
| T5 |
653-871 |
Sentence |
denotes |
We have developed a novel method for the synthesis of 1,2-cis-2-amino glycosides via nickel-catalyzed α-selective glycosylation with C(2)-N-substituted benzylidene D-glucosamine and galactosamine trichloroacetimidates. |
| T6 |
872-1029 |
Sentence |
denotes |
These glycosyl donors are capable of coupling to a wide variety of alcohols to provide glycoconjugates in high yields with excellent levels of α-selectivity. |
| T7 |
1030-1252 |
Sentence |
denotes |
Additionally, only a substoichiometric amount of nickel (5-10 mol %) is required for the reaction to occur at 25 °C. The current nickel method relies on the nature of the nickel-ligand complex to control the α-selectivity. |
| T8 |
1253-1371 |
Sentence |
denotes |
The reactive sites of the nucleophiles or the nature of the protecting groups have little effect on the α-selectivity. |
| T9 |
1372-1545 |
Sentence |
denotes |
This methodology has also been successfully applied to both disaccharide donors and acceptors to provide the corresponding oligosaccharides in high yields and α-selectivity. |
| T10 |
1546-1709 |
Sentence |
denotes |
The efficacy of the nickel procedure has been further applied toward the preparation of heparin disaccharides, GPI anchor pseudodisaccharides, and α-GluNAc/GalNAc. |
| T11 |
1710-1919 |
Sentence |
denotes |
Mechanistic studies suggest that the presence of the substituted benzylidene functionality at the C(2)-amino position of glycosyl donors is crucial for the high α-selectivity observed in the coupling products. |
| T12 |
1920-2057 |
Sentence |
denotes |
Additionally, the α-orientation of the C(1)-trichloroacetimidate group on glycosyl donors is necessary for the coupling process to occur. |
