210832-77-2

Upstream product

• 58341-67-6 methyl 2,4-di-O-benzyl-α-D-mannopyranoside 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 254444-67-2 Methyl 2,4-di-O-benzyl-3-O-[3,4,6-tri-O-benzyl-2-O-(2',2',2'-trichloroethoxycarbonyl)-α-D-mannopyranosyl]-6-O-tert-butyldiphenylsilyl-α-D-mannopyranoside 
• 466646-15-1 ((2R,3R,4R,5R,6S)-3,5-Bis-benzyloxy-4-iodo-6-methoxy-tetrahydro-pyran-2-ylmethoxy)-tert-butyl-diphenyl-silane 
• 254444-13-8 Methyl 2,4-di-O-benzyl-3-O-[3,4,6-tri-O-benzyl-2-O-(2',2',2'-trichloroethoxycarbonyl)-α-D-mannopyranosyl]-α-D-mannopyranoside 
• 466646-18-4 [(2R,3S,4R,5S,6S)-3,5-Bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-4-yl]-methanol 
• 466646-17-3 ((2R,3S,5S,6S)-3,5-Bis-benzyloxy-6-methoxy-4-methylene-tetrahydro-pyran-2-ylmethoxy)-tert-butyl-diphenyl-silane 
• 210832-78-3 Acetic acid (2R,3S,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(2R,3R,4S,5S,6S)-3,5-bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-6-methoxy-tetrahydro-pyran-4-yloxy]-tetrahydro-pyran-3-yl ester 

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.

Synthesis of glycans from the glycodelins: Two undeca-, two deca-, three nona-, an octa- and a heptasaccharide

The concise synthesis of nine diantennary oligosaccharides by chemical and chemoenzymatic protocols is presented. The compounds display Lewis X, Lewis Y, sialyl Lewis X and T-antigen epitopes supported on a 3,6-branched trimannose core. A chemical approach was adopted for the synthesis of the unsymmetrically decorated structures and those that could not be accessed by enzymatic decoration of a core heptasaccharide.