676263-72-2

Upstream product

• 100-52-7 benzaldehyde 
• 132871-96-6 (2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triol 
• 1125-88-8 benzaldehyde dimethyl acetal 

Downstream Products

• 389119-51-1 (2R,3R,4S,5R,6R)-3,5-Bis-benzyloxy-2-hydroxymethyl-6-pent-4-enyloxy-tetrahydro-pyran-4-ol 
• 389119-52-2 4-pentenyl 3,6-di-O-acetyl-2,4-di-O-benzyl-β-D-galactopyranoside 
• 389119-75-9 2-propenyl 2,4-di-O-benzyl-3-O-(2,4-di-O-benzyl-β-D-galactopyranosyl)-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of β-1,4-Linked Galactan Side-Chains of Rhamnogalacturonan I

The synthesis of linear- and (1→6)-branched β-(1→4)-d-galactans, side-chains of the pectic polysaccharide rhamnogalacturonan I is described. The strategy relies on iterative couplings of n-pentenyl disaccharides followed by a late stage glycosylation of a common hexasaccharide core. Reaction with a covalent linker and immobilization on N-hydroxysuccinimide (NHS)-modified glass surfaces allows the generation of carbohydrate microarrays. The glycan arrays enable the study of protein–carbohydrate interactions in a high-throughput fashion, demonstrated herein with binding studies of mAbs and a CBM.

Synthesis of a set of di- and tri-sulfated galabioses

Among cell-adhesion molecules, L-selectin recognizes sulfated sLex with relatively low affinity. Here, we aimed at artificial mimics by synthesizing a set of di- and tri-sulfated galabioses, which may surpass the affinity of sulfated sLex. As a strategy to obtain 3′,6′,6-tri-O-sulfogalabioses, regioselective reductive cleavage of 4,6- and 4′,6′-di-O-benzylidenegalabioses was employed. Two suitably protected galactose precursors were conjugated to yield α and β anomers (48 and 18%, respectively) by using a pentenyl galactoside donor and iodinium di-sym-collidine perchlorate as the catalyst. For synthesizing the 3′,6-di-O-sulfogalabiose, however, a trichloroacetimidate donor was superior (52%) to the pentenyl one (30%).