389119-75-9

Upstream product

• 71925-95-6 allyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 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 
• 676263-72-2 pent-4-enyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 2595-07-5 allyl β-D-galactopyranoside 

Relevant academic research and scientific papers

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%).