81927-58-4

Basic information

• Product Name: methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
• Synonyms: methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS NO: 81927-58-4
• Molecular Weight: 501.536
• Mol File: 81927-58-4.mol

Chemical Properties

• CAS DataBase Reference: methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside(81927-58-4)
• EPA Substance Registry System: methyl 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside(81927-58-4)

Safety Data

• Hazardous Substances Data: 81927-58-4(Hazardous Substances Data)

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 76101-13-8 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 10028-45-2 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide 
• 76101-14-9 methyl-2-desoxy-2-phthalimido-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 81927-56-2 methyl 4,6-O-benzylidene-2-deoxy-2-phthalimide-β-D-glucopyranoside 

Downstream Products

• 97242-85-8 methyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 97242-79-0 methyl 3,6-di-O-benzyl-2-deoxy-2-N-phthalimido-β-D-glucopyranoside 
• 97242-87-0 methyl 3-O-benzyl-2-deoxy-2-phthalimido-4,6-di-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 
• 151342-40-4 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 
• 97242-83-6 methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-2-deoxy-β-D-glucopyranoside 
• 97242-86-9 methyl 3-O-benzyl-2-deoxy-2-phthalimido-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 
• 97242-81-4 methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 97242-88-1 methyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-(2,3,4-tri-O-benzyl-α-L-fucopyranosyl)-β-D-glucopyranoside 
• 97242-82-5 methyl 2-acetamido-4-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2-deoxy-β-D-glucopyranoside 
• 97242-84-7 methyl 2-acetamido-4-O-(2'-acetamido-2'-deoxy-β-D-glucopyranosyl)-2-deoxy-6-O-(α-L-fucopyranosyl)-β-D-glucopyranoside 

Relevant articles and documents

Selectively Deoxyfluorinated N-Acetyllactosamine Analogues as 19F NMR Probes to Study Carbohydrate-Galectin Interactions

Galectins are widely expressed galactose-binding lectins implied, for example, in immune regulation, metastatic spreading, and pathogen recognition. N-Acetyllactosamine (Galβ1-4GlcNAc, LacNAc) and its oligomeric or glycosylated forms are natural ligands of galectins. To probe substrate specificity and binding mode of galectins, we synthesized a complete series of six mono-deoxyfluorinated analogues of LacNAc, in which each hydroxyl has been selectively replaced by fluorine while the anomeric position has been protected as methyl β-glycoside. Initial evaluation of their binding to human galectin-1 and -3 by ELISA and 19F NMR T2-filter revealed that deoxyfluorination at C3, C4′ and C6′ completely abolished binding to galectin-1 but very weak binding to galectin-3 was still detectable. Moreover, deoxyfluorination of C2′ caused an approximately 8-fold increase in the binding affinity towards galectin-1, whereas binding to galectin-3 was essentially not affected. Lipophilicity measurement revealed that deoxyfluorination at the Gal moiety affects log P very differently compared to deoxyfluorination at the GlcNAc moiety.