125790-91-2

Upstream product

• 389119-56-6 2-propenyl 3-O-(4-methoxybenzyl)-β-D-galactopyranoside 
• 100-39-0 benzyl bromide 
• 2595-07-5 allyl β-D-galactopyranoside 
• 71925-95-6 allyl 4,6-O-benzylidene-β-D-galactopyranoside 
• 389119-60-2 allyl 2,4,6-tribenzyl-3-p-methoxybenzyl-β-D-galactopyranoside 

Downstream Products

• 389119-79-3 Acetic acid (2R,3S,4S,5R,6R)-4-((2R,3R,4S,5S,6R)-4-acetoxy-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-6-allyloxy-3,5-bis-benzyloxy-tetrahydro-pyran-2-ylmethyl ester 
• 389119-80-6 2-propenyl 2,4-O-benzyl-3-O-(2,4,6-tri-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 389119-61-3 3-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranosyl trichloroacetimidate 
• 127875-29-0 Acetic acid (2R,3S,4S,5R,6R)-3,5-bis-benzyloxy-2-benzyloxymethyl-6-hydroxy-tetrahydro-pyran-4-yl ester 
• 471930-55-9 dibutyl 2,4,6-tribenzyl-3-levulinoyl-β-D-galactopyranoside phosphate 
• 471930-63-9 2,4,6-tribenzyl-3-levulinoyl-α-D-galactopyranosyl trichloroacetimidate 
• 125790-92-3 2-propenyl 6-O-acetyl-2,4,6-tri-O-benzyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Linear synthesis of the tumor-associated carbohydrate antigens Globo-H, Ssea-3, and Gb3

The tumor-associated carbohydrate antigens Globo-H, SSEA-3, and Gb3 were synthesized in a linear fashion using glycosyl phosphate monosaccharide building blocks. All of the building blocks were prepared from readily available common precursors. The difficult α-(1→-4-cis)-galactosidic linkage was installed using a galactosyl phosphate donor with high selectivity. Introduction of the β-galactosamine unit required the screening a variety of amine protecting groups to ensure good donor reactivity and protecting group compatibility. An N-trichloroacetyl-protected galactosamine donor performed best for the installation of the β-glycosidic linkage. Conversion of the trichloroacetyl group to the N-acetyl group was achieved under mild conditions, fully compatible with the presence of multiple glycosidic bonds. This synthetic strategy is expected to be amenable to the synthesis of the globo-series of tumor antigens on solid-support.

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%).