37111-91-4

Upstream product

• 100-39-0 benzyl bromide 
• 10257-28-0 D-Galactose 
• 282089-13-8 allyl 3,4-O-cyclohexylidene-α-D-galactopyranoside 
• 81713-32-8 allyl 3,4-O-isopropylidene-α-D-galactopyranoside 
• 282089-15-0 allyl 3,4-O-cyclohexylidene-2,6-di-O-benzyl-α-D-galactopyranoside 
• 81713-34-0 Allyl 2,6-di-O-benzyl-3,4-O-isopropylidene-α-D-galactopyranoside 
• 48149-72-0 (2S,3R,4S,5R,6R)-2-Allyloxy-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 

Downstream Products

• 149001-83-2 Allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α-D-galactopyranoside 
• 178319-02-3 allyl 2,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-galactopyranoside 
• 282089-17-2 allyl 2,6-di-O-benzyl-3-O-(2,3,4,6-tetra-O-benzyl-α-D-galactopyranosyl)-α-D-galactopyranoside 
• 607720-98-9 allyl 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl-(1->3)-2,6-di-O-benzyl-α-D-galactopyranoside 
• 61893-74-1 allyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside 
• 81713-36-2 allyl 4-O-benzoyl-2,6-di-O-benzyl-3-O-(2-methoxyethoxy)methyl-α-D-galactopyranoside 
• 81713-37-3 allyl 2,4,6-tri-O-benzyl-3-O-(2-methoxyethoxy)methyl-α-D-galactopyranoside 
• 61236-87-1 allyl 2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 178319-05-6 allyl 2,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-glucopyranoside 
• 178319-07-8 allyl 3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranoside 

Relevant academic research and scientific papers

Synthesis of the blocked pentasaccharide derivative related to the repeating unit of the O-antigen from Shigella dysenteriae type 3 in the form of its allyl glycoside

Starting from D-galactosamine hydrochloride, D-galactose and D-glucose, the tetrasaccharide derivative allyl 2,3,6-tri-O-benzyl-4-O-[methyl (R)-2-propanoate]-β-D-glucopyranosyl-(1→6)-2,3, 4-tri-O-benzyl-α-D-glucopyranosyl-(1→4)-2,6-di-O-benzyl-3-O-(3,4, 6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-galactopyranosyl) -α-D-galactopyranoside has been synthesized via block synthesis strategy, with one of the blocks containing a methyl (R)-2-propanoate group. Manipulation of protecting groups of this tetrasaccharide derivative followed by its reaction with a galactofuranoside donor afforded the desired pentasaccharide derivative in the form of its allyl glycoside related to the reapeating unit of Shigella dysenteriae type 3.

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.

"STANDARDIZED INTERMEDIATES" FOR OLIGOSACCHARIDE SYNTHESIS. PRECURSORS OF D-GALACTOPYRANOSE RESIDUES HAVING CHAIN EXTENSION AT POSITION 3, OR POSITIONS 3 AND 2

A series of 2-O-benzoyl-4,6-di-O-benzyl-α-D-galactopyranosyl halides carrying either a second benzoyl group (8a, 12a) or a selectively removable, temporary protecting group (8b-d, 12b) at position 3 was synthesized from allyl α-D-galactopyranoside (1).The