1350309-52-2

Upstream product

• 13154-24-0 triisopropylsilyl chloride 
• 165307-54-0 methyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside 

Downstream Products

• 1350309-54-4 methyl 4,6-O-benzylidene-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside 
• 1350309-55-5 methyl 3-O-benzyl-4,6-O-benzylidene-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside 
• 1350309-56-6 methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside 
• 1350309-64-6 4-methoxyphenyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzyl-α-D-xylopyranoside 
• 1350309-66-8 2-O-acetyl-3,6-di-O-benzyl-4-O-triisopropylsilyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-D-xylopyranosyl fluoride 
• 1350309-45-3 methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-4-O-triisopropylsilyl-α-D-mannopyranoside 
• 1350309-46-4 methyl 3,4,6-tri-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside 
• 1350309-62-4 C₄₁H₅₈O₁₁Si 
• 1350309-63-5 C₆₂H₇₆O₁₁Si 
• 1350309-49-7 4-methoxyphenyl 3,6-di-O-benzyl-4-O-triethylsilyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside 
• 1350309-50-0 4-methoxyphenyl 2,4-di-O-acetyl-3,6-di-O-benzyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside 
• 1350309-51-1 4-methoxyphenyl 2-O-acetyl-3,6-di-O-benzyl-4-O-triisopropylsilyl-β-D-mannopyranosyl-(1->4)-2,3-di-O-benzoyl-α-D-xylopyranoside 
• 1350309-53-3 methyl 4,6-O-benzylidene-2-O-(2-naphthylmethyl)-1-thio-3-O-triisopropylsilyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Synthetic study and structural analysis of the antifreeze agent xylomannan from Upis ceramboides

The novel antifreeze factor, xylomannan, first isolated from the freeze-tolerant Alaskan beetle Upis ceramboides, demonstrates a high degree of thermal hysteresis, comparable to that of the most active insect antifreeze proteins. Although the presence of a lipid component in this factor has not yet been verified, it has been proposed that the glycan backbone consists of a β-d-mannopyranosyl-(1→4)-β-d-xylopyranose-disaccharide-repeating structure according to MS and NMR analyses. In this contribution, we report the stereoselective synthesis of the tetrasaccharide β-d-mannopyranosyl- (1→4)-β-d-xylopyranosyl-(1→4)-β-d-mannopyranosyl-(1→4) -d-xylopyranoside, a structural component of xylomannan. Our synthesis features the use of 2-naphthylmethyl (NAP)-ether-mediated intramolecular aglycon delivery (IAD) as the key reaction in obtaining β-mannopyranoside stereoselectively. Various donors for NAP-IAD were tested to determine the most suitable for the purposes of this synthesis. Fragment coupling between a disaccharyl fluoride and a disaccharide acceptor obtained from a common β-d-mannopyranosyl-(1→4)-β-d-xylopyranoside derivative was successfully carried out to afford the desired tetrasaccharide in the presence of Cp2HfCl2-AgClO4. Structural analysis of the resulting synthetic tetrasaccharide using NMR techniques and molecular modeling was performed in order to demonstrate the presence of the proposed xylomannan linkages in this molecule.