913061-13-9

Upstream product

• 76-83-5 trityl chloride 
• 476196-98-2 (2R,3R,4S,5R,6R)-2-(3-azidopropoxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 
• 819053-49-1 1-O-(3-azidopropyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 
• 90214-67-8 (2R,3S,4S,5R,6R)-2-(acetoxymethyl)-6-(3-bromopropoxy)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 25878-60-8 D-galactose pentaacetate 

Downstream Products

• 913060-97-6 3-azidopropyl 2-O-benzoyl-4-O-benzyl-3-O-(9-fluorenylmethoxycarbonyl)-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 
• 913060-96-5 3-azidopropyl 2-O-benzoyl-4,6-O-benzylidene-3-O-(9-fluorenylmethoxycarbonyl)-β-D-galactopyranosyl-(1->6)-2,3,4-tri-O-benzoyl-β-D-galactopyranoside 
• 913060-94-3 3-azidopropyl 2,3,4-tri-O-benzoyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of 3,6-branched arabinogalactan-type tetra- and hexasaccharides for characterization of monoclonal antibodies

Synthesis of tetra- and hexasaccharides built up from a β-(1→6)-linked galactopyranosyl backbone with arabinofuranosyl side chains at position 3 and with a 3-aminopropyl spacer related to arabinogalactans is described. These oligosaccharides were prepared

Practical approach for the stereoselective introduction of β-arabinofuranosides

A practical approach for the stereoselective introduction of β-arabinofuranosides has been developed on the basis of locking an arabinosyl donor in a conformation in which nucleophilic attack from the β face is favored. The new glycosyl donor was designed by analyzing optimized geometries of low-energy conformers of the arabinofuranosyl oxacarbenium ion. The Newman projection of the E3 conformer indicated that nucleophilic attack from the α face is disfavored because an eclipsed H-2 will be encountered. On the other hand, an approach from the β face was expected to be more favorable, because it will experience only staggered substituents. The arabinofuranosyl oxacarbenium ion could be locked in the E3 conformation by employing a 3,5-O-di-tert-butylsilane protecting group, which places C-5 and O-3 in a pseudoequatorial orientation, resulting in a perfect chair conformation of the protecting group. The new glycosyl donor gave excellent β selectivities in a range of glycosylations with glycosyl acceptors having primary and secondary alcohols. The attractiveness of the new methodology was demonstrated by the chemical synthesis of a fragment of arabinogalactan, which is an important constituent of the primary plant cell wall.