466646-29-7

Upstream product

• 466646-35-5 Trimethyl-[3-((2R,3R,4S,5S,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-1-ynyl]-silane 
• 466646-26-4 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-ethynyl-α-D-mannopyranoside 
• 466646-27-5 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-vinyl-α-D-mannopyranoside 
• 617-04-9 (2R,3S,4S,5S,6S)-2-(hydroxymethyl)-6-methoxytetrahydro-2H-pyran-3,4,5-triol 
• 221545-35-3 ((2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-6-methoxytetrahydro-2H-pyran-2-yl)methyl trifluoromethanesulfonate 
• 131089-34-4 3-O-benzoyl-6-O-(t-butyldiphenyl)silyl-α-D-mannopyranoside 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 40653-17-6 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-formyl-α-D-mannopyranoside 
• 466646-28-6 methyl 2,3,4-tri-O-benzyl-6-deoxy-6-C-(1'-(2',3',4',6'-tetra-O-benzyl-1'deoxy-α-D-mannopyranosyl)(oxythiocarbonylimidazolyl)methyl)-α-D-mannopyranoside 

Relevant 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

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.