466646-17-3

Upstream product

• 210832-77-2 Methyl 2,4-di-O-benzyl-6-O-(tert-butyldiphenylsilyl)-α-D-mannopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 58341-67-6 methyl 2,4-di-O-benzyl-α-D-mannopyranoside 

Downstream Products

• 466646-18-4 [(2R,3S,4R,5S,6S)-3,5-Bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-4-yl]-methanol 

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.