117149-98-1

Upstream product

• 34820-01-4 methyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside 
• 4291-68-3 (2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-chloro-tetrahydro-pyran 
• 125411-99-6 ethyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 55722-49-1 ethyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-galactopyranoside 
• 56245-60-4 ethyl 1-thio-β-D-galactopyranoside 
• 98-88-4 benzoyl chloride 

Downstream Products

• 96103-31-0 methyl 2,3,6-tri-O-benzoyl-4-O-α-D-galactopyranosyl-β-D-galactopyranoside 
• 117012-07-4 methyl 2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 345320-59-4 Methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 117124-68-2 methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-fucopyranoside 
• 117124-67-1 methyl 2,3-di-O-benzoyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-fucopyranoside 
• 117124-66-0 methyl 2,3-di-O-benzoyl-6-deoxy-6-iodo-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 96103-00-3 methyl 2,3-di-O-benzoyl-4-O-(4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-fucopyranoside 
• 96102-98-6 methyl 2,3-di-O-benzoyl-4-O-(4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 96102-99-7 methyl 2,3-di-O-benzoyl-4-O-(4,6-O-benzylidene-α-D-galactopyranosyl)-6-deoxy-6-iodo-β-D-galactopyranoside 
• 96103-33-2 methyl 2,3,6-tri-O-benzoyl-4-O-(4,6-O-benzylidene-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 96103-02-5 methyl 2,3-di-O-benzoyl-4-O-(2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-galactopyranosyl)-β-D-fucopyranoside 
• 96120-70-6 methyl 2,3,6-tri-O-benzoyl-4-O-(2,3-di-O-acetyl-4-O-benzoyl-6-bromo-6-deoxy-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 345320-63-0 Methyl 2,3-di-O-acetyl-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-6-O-(p-tolylsulfonyl)-β-D-galactopyranoside 
• 345320-65-2 Methyl 2,3-di-O-acetyl-6-azido-6-deoxy-4-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis and structure-activity relationships of di- and trisaccharide inhibitors for Shiga-like toxin Type 1

The syntheses of galabiose and Pk-trisaccharide analogues in which selected hydroxy groups are replaced by O-methyl, amino deoxy, acetamido deoxy, and carboxyalkyl groups are reported. The ability of these inhibitors to block E. coli verotoxin 1 binding to its mammalian cell-surface receptor are evaluated by a solid-phase competition assay. The synthesis of a biotinylated glycoconjugate for this assay is described, wherein a Pk-trisaccharide tether derivative 70 is constructed and covalently attached to bovine serum albumin followed by biotinylation. Galabiose derivatives 4 and 5 that contain a carboxymethyl or carboxyethyl substituent at O-2 of the β-galactose residue show 15-20-fold activity gains over the methyl glycoside of galabiose. This enhanced activity is not observed for the corresponding carboxymethyl-substituted Pk-trisaccharide analogue 13. The inhibition data are rationalized with the solved crystal structure for verotoxin 1 complexed with a Pk-trisaccharide analogue and provide insight for the design of dimeric inhibitors that can exploit the unique binding-site distribution of the toxin's B subunit. This discussion provides a further example of the important role played by ordered water molecules in sugar-protein complexes.

The in Situ Activation of Thioglycosides with Bromine: An Improved Glycosylation Method

A one-step conversion of thioglycosides into 1,2-trans- or 1,2-cis-O-glycosides was accomplished, in situ, by treatment with bromine in the presence of a glycosyl acceptor and a promoter such as silver triflate or mercuric cyanide.This mild "one-pot" proc