215381-22-9

Upstream product

• 843674-45-3 7-O-acetyl-1,6-anhydro-L-glycero-β-D-manno-heptopyranose 
• 215381-17-2 1,6-anhydro-2,3-O-isopropylidene-L-glycero-β-D-manno-heptopyranose 
• 215381-41-2 1,6-anhydro-2,3,4,7-tetra-O-benzyl-L-glycero-β-D-manno-heptopyranose 
• 60687-60-7 1,6-anhydro-L-glycero-β-D-manno-heptopyranose 
• 14218-11-2 2,3,4,6-tetra-O-benzoylglucosyl bromide 
• 215381-19-4 (2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)-7-O-acetyl-1,6-anhydro-2,3-O-isopropylidene-L-glycero-β-D-manno-heptopyranose 
• 215381-18-3 7-O-acetyl-1,6-anhydro-2,3-O-isopropylidene-L-glycero-β-D-manno-heptopyranose 
• 201135-20-8 methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-α-D-manno-oct-7-enopyranoside 
• 34212-64-1 methyl 2,3,4-tri-O-benzyl-α-D-mannopyranoside 
• 40653-15-4 methyl 2,3,4-tri-O-benzyl-α-D-manno-hexodialdo-1,5-pyranoside 
• 843674-44-2 7-O-acetyl-1,6-anhydro-2,3,4-tri-O-benzyl-L-glycero-β-D-manno-heptopyranose 
• 843674-43-1 1,6-anhydro-2,3,4-tri-O-benzyl-L-glycero-β-D-manno-heptopyranose 
• 843674-42-0 1,6-anhydro-2,3,4-tri-O-benzyl-7,8-dideoxy-β-D-manno-oct-7-enopyranose 
• 100-39-0 benzyl bromide 

Downstream Products

• 1240564-13-9 6-O-allyl-2-O-benzoyl-4,7-di-O-benzyl-3-O-chloroacetyl-L-glycero-α-D-manno-heptopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-7-O-acetyl-1,6-anhydro-2-O-benzyl-L-glycero-α-D-manno-heptopyranose 
• 1240564-12-8 6-O-allyl-4,7-di-O-benzyl-2,3-O-isopropylidene-L-glycero-β-D-manno-heptopyranosyl-(1->3)-[2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl-(1->4)]-7-O-acetyl-1,6-anhydro-2-O-benzyl-L-glycero-α-D-manno-heptopyranose 
• 215381-30-9 (2,3,4,6,7-penta-O-benzoyl-L-glycero-α-D-manno-heptopyranosyl)-(1->3)-<(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(1->4)>-7-O-acetyl-1,6-anhydro-2-O-benzyl-L-glycero-β-D-manno-heptopyranose 

Relevant academic research and scientific papers

Synthesis of the branched trisaccharide L-glycero-α-D-manno- heptopyranosyl-(1 → 3)- [β-D-glucopyranosyl-(1 → 4)]-L-glycero-α-D-manno-heptopyranose, protected to allow flexible access to Neisseria and Haemophilus LPS inner core structures

An efficient synthesis of the protected branched trisaccharide (2′S,3′S)-(7-O-benzyl-6-O-chloroacetyl-3,4-O-(2′, 3′-dimethoxybutane-2′,3′-diyl)-2-O-p-methoxybenzyl-L-glycero- α-D-manno-heptopyranosyl)-(1 → 3)-[(2,3,4,6-tetra-O-benzoyl-β-D- glucopyranosyl)

Synthesis of a branched heptose- and kdo-containing common tetrasaccharide core structure of haemophilus influenzae lipopolysaccharides via a l,6-anhydro-l-glycero-β-d-manno-heptopyranose intermediate

The synthesis of a common tetrasaccharide core structure of Haemophilus influenzas lipopolysaccharides, β-D-glucopyranosyl-(1→4)-[L-glycero-α.-D-manno-heptopyranosyl- (1→3)]-L-glycero-α-Dmanno-heptopyranosyl-(1→5)-3-deoxy-α- D-manno-octulopyrahoside, and the trisaccharide β-D-glucopyranosyl(1→4)-[L-glycero-α-D-manno-heptopyranosyl- (1→3)]-L-glycero-α-D-manno-heptopyranoside is described. The oligosaccharides are synthesized as glycosides of a bifunctional spacer, 2-(4-aminophenyDethanol, to allow the subsequent formation of immunogenic glycoconjugates, which will be evaluated as well-defined glycoconjugate vaccine candidates. The syntheses of the 3,4branched structures were accomplished using a 1,6-anhydro-L-glycero-β-D-manno-heptopyranose intermediate to diminish the steric crowding between the 3- and 4-substituent. This intermediate was effectively synthesized from a mannose precursor via a stereoselective one-carbon elongation using a Barbier reaction (which was found to be more convenient than a Grignard reaction) and anhydro bridge formation through an internal glycosylation of a 6-O-trimethylsilylated ethyl thioheptoside using NIS/TfOH as a promoter. The 3- and 4-substituent were readily introduced into the 1,6-anhydro intermediate by glycosylation reactions using thioglycosides as donors and NIS/TfOH as a promoter, a task which has not been possible using acceptors with equatorial 3,4substituents. Acetolysis of the anhydro bridge followed by conversion into the ethyl thioglycoside afforded a trisaccharide donor, which, in NIS/TfOH-promoted couplings to the spacer and to a Kdo acceptor followed by deprotection, efficiently gave the two target compounds.