282089-18-3

Basic information

• Product Name: allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside
• Synonyms: allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside
• CAS NO: 282089-18-3
• Molecular Weight: 923.113
• Mol File: 282089-18-3.mol

Chemical Properties

• CAS DataBase Reference: allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside(282089-18-3)
• EPA Substance Registry System: allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside(282089-18-3)

Safety Data

• Hazardous Substances Data: 282089-18-3(Hazardous Substances Data)

Upstream product

• 74808-09-6 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl trichloroacetimidate 
• 125790-89-8 allyl 2,6-di-O-benzyl-β-D-galactopyranoside 
• 112344-80-6 2-propenyl 2,3,4,6-tetra-O-benzyl-α-D-glactopyranoside 
• 2595-07-5 allyl β-D-galactopyranoside 
• 6386-24-9 2,3,4,6-tetra-O-benzyl-D-galactopyranose 
• 100-39-0 benzyl bromide 
• 48149-72-0 (2S,3R,4S,5R,6R)-2-Allyloxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 
• 282089-14-9 allyl 3,4-O-cyclohexylidene-β-D-galactopyranoside 

Downstream Products

• 282089-20-7 (3-tosyloxy)propyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 282089-21-8 (3-azido)propyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 584-30-5 3-O-α-D-galactopyranosyl-α-D-galactopyranose 
• 282089-22-9 (2-hydroxy)propyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 282089-19-4 (3-hydroxy)propyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-β-D-galactopyranoside 

Relevant articles and documents

A novel synthesis of α-D-Galp-(1→3)-β-D-Galp-1-Ο-(CH2) 3-NH2, its linkage to activated matrices and absorption of anti-αGal xenoantibodies by affinity columns

Pig organs transplanted into primates are rapidly rejected because of the interaction between Galα(1→3)Gal epitopes carried by the graft and natural antibodies (anti-αGal antibodies) present in the blood of the recipient. This report describes a simplified synthesis of the xenogeneic disaccharide and its linkage to activated gel matrices. The digalactosides α-D-Galp-(1→3)-α,β-D-Galp-Galp were synthesized by the condensation of the trichloroacetimidoyl 2,3,4,6-tetra-Ο-benzyl-β-D-galactopyranoside donor with the 3,4-unprotected allyl 2,6-di-Ο-benzyl-α- or β-D-galactopyranoside acceptor precursor. Deallylation and hydrogenolysis led to the free digalactoside, whereas hydrogenolysis alone resulted in the 1-Ο-propyl digalactoside. Both products were tested by inhibition ELISA of natural anti-Gala(1→3)Gal antibodies. The α-D-Galp-(1→3)-β-D-Galp-OPr was found to be the best inhibitor. Thus, the allyl group of the partially benzylated α-D-Galp-(1→3)-β-D-Galp-OAll was engineered, via the hydroxy-, the tosyloxy- and the azidopropyl intermediates, into an aminopropyl group amenable to binding to N-hydroxysuccinimide-activated agarose gel matrices in order to obtain specific immunoabsorption columns. Columns made of gel substituted with 5 μmol of disaccharide per milliliter were found efficient for the immunoabsorption of anti-αGal antibodies from human plasma.