251456-75-4Relevant academic research and scientific papers
Application of the anomeric samarium route for the convergent synthesis of the C-linked trisaccharide α-D-Man-(1→3)-[α-D-Man-(1→6)]-D-Man and the disaccharides α-D-Man-(1→3)-D-Man and α-D-Man-(1→6)-D-Man
Mikkelsen, Lise Munch,Krintel, Sussie Lerche,Jimenez-Barbero, Jesus,Skrydstrup, Troels
, p. 6297 - 6308 (2007/10/03)
Studies are reported on the assembly of the branched C-trisaccharide, α-D-Man-(1→3)-[α-D-Man-(1→6)]-D-Man, representing the core region of the asparagine-linked oligosaccharides. The key step in this synthesis uses a SmI2-mediated coupling of two mannosylpyridyl sulfones to a C3,C6-diformyl branched monosaccharide unit, thereby assembling all three sugar units in one reaction and with complete stereocontrol at the two anomeric carbon centers. Subsequent tin hydride-based deoxygenation followed by a deprotection step produces the target C-trimer. In contrast to many of the other C-glycosylation methods, this approach employes intact carbohydrate units as C-glycosyl donors and acceptors, which in many instances parallels the well-studied O-glycosylation reactions. The synthesis of the C-disaccharides α-D-Man-(1→3)-D-Man and α-D-Man-(1→6)-D-Man is also described, they being necessary for the following conformational studies of all three carbohydrate analogues both in solution and bound to several mannose-binding proteins.
A convergent synthesis of α-C-1,3-mannobioside via SmI2-promoted C-glycosylation
Krintel, Sussie L.,Jimenez-Barbero, Jesus,Skrydstrup, Troels
, p. 7565 - 7568 (2007/10/03)
The C-disaccharide of α-1,3-mannobioside has been synthesized via the direct coupling of a mannosyl pyridyl sulfone and a C-formyl branched sugar with the one electron reducing agent, SmI2. The sterically hindered alcohol obtained in this coupl
