346420-68-6

Basic information

• Product Name: Prop-2-ynyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside
• Synonyms: Prop-2-ynyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside
• CAS NO: 346420-68-6
• Molecular Weight: 798.752
• Mol File: 346420-68-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: Prop-2-ynyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Prop-2-ynyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside(346420-68-6)
• EPA Substance Registry System: Prop-2-ynyl (2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-(1->3)-4-O-acetyl-2,6-di-O-benzoyl-β-D-galactopyranoside(346420-68-6)

Safety Data

• Hazardous Substances Data: 346420-68-6(Hazardous Substances Data)

Upstream product

• 346420-65-3 C₃₈H₄₂O₁₉ 
• 107-19-7 propargyl alcohol 

Relevant articles and documents

Synthesis of clustered xenotransplantation antagonists using palladium-catalyzed cross-coupling of prop-2-ynyl α-D-galactopyranoside

Hyperacute rejection of pig liver transplantation can be antagonized using high affinity anti α-galactoside epitopes (Galα1-3Galβ, Galili antigen). To this end, clusters containing the Galili antigen were synthesized using palladium cross-coupling reactions. Thus, benzyl 3-(O-α-D-galactopyranosyl)-β-D-galactopyranoside derivative 6 was prepared using perbenzylated thiophenyl β-D-galactopyranosyl donor 5 and benzyl 2,6-di-O-benzoyl-α-D-galactopyranosyl acceptor 3. Aglycone interchange from benzyl to prop-2-ynyl disaccharide 8 was successively achieved by hydrogenolysis, peracetylation, regioselective anomeric de-O-acetylation, trichloroacetimidate activation, and finally coupling to propargyl alcohol with triflic acid. The resulting prop-2-ynyl disaccharide 8 was transformed in high yields (>85%) into dimer 10, trimer 12, and tetramer 17 using oxidative homocoupling (10) and palladium-catalyzed aryl iodide cross-coupling (12,17), respectively. Ester protecting group removal under transesterification conditions afforded fully deprotected α-Gal clusters.