324768-46-9Relevant 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 highly convergent synthesis of a branched C-trisaccharide employing a double SmI2-promoted C-glycosylation
Mikkelsen,Krintel,Jimenez-Barbero,Skrydstrup
, p. 2319 - 2320 (2007/10/03)
The branched C-trisaccharide analogue of α-D-Man-(1→3)-[α-D-Man-(1→6)]-D-Man has been synthesised by the SmI2-mediated coupling of two mannosyl pyridyl sulfone units to a monosaccharide dialdehyde. This approach represents a highly convergent s
