653597-40-1

Upstream product

• 1125-88-8 benzaldehyde dimethyl acetal 
• 1446474-56-1 2-azidoethyl 2-O-acetyl-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside 
• 1446474-55-0 phenyl 2-O-acetyl-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-α-D-mannopyranoside 
• 168138-26-9 phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside 
• 155196-97-7 2-azidoethyl α-D-mannopyranoside 
• 140428-83-7 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 824-94-2 p-methoxybenzyl chloride 
• 653597-39-8 2-azidoethyl 4,6-O-benzylidene-α-D-mannopyranoside 

Downstream Products

• 1446474-57-2 2-azidoethyl (4,6-O-benzylidene-2,3-di-O-(p-methoxybenzyl)-β-D-mannopyranosyl)-(1→2)-4,6-O-benzylidene-3-O-(p-methoxybenzyl)-α-D-mannopyranoside 
• 653597-57-0 2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(3-O-allyl-4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 653597-53-6 2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(6-O-acetyl-3-O-allyl-4-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 653597-58-1 2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 653597-54-7 2-azidoethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1->2)-(6-O-acetyl-4-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 653597-42-3 2-azidoethyl 2,4,6-tri-O-benzyl-3-O-(p-methoxybenzyl)-α-D-mannopyranoside 
• 653597-43-4 2-azidoethyl 2,4,6-tri-O-benzyl-α-D-mannopyranoside 
• 653597-41-2 2-azidoethyl 3-O-(p-methoxybenzyl)-α-D-mannopyranoside 

Relevant academic research and scientific papers

Influence of the reducing-end anomeric configuration of the Man9epitope on DC-SIGN recognition

High-mannose (Man9GlcNAc2) is the main carbohydrate unit present in viral envelope glycoproteins such as gp120 of HIV and the GP1 of Ebola virus. This oligosaccharide comprises the Man9 epitope conjugated to two terminal N-acetylglucosamines by otherwise

Chemistry and biology of oligovalent β-(1→2)-linked oligomannosides: New insights into carbohydrate-based adjuvants in immunotherapy

A series of oligovalent carbohydrate assemblies (ranging from mono- to pentavalent), derived from three structurally different β-linked or β-(1→2)-linked mannosides, has been chemically synthesized, and the respective compounds have been biologically evaluated in order to investigate their immunostimulatory properties. The Crich methodology for β-mannosylation was successfully utilized to introduce the β-linkages, and a click chemistry protocol was utilized to generate the oligovalent derivatives. A convenient protecting group strategy involving the simultaneous use of both p-methoxybenzyl and benzylidene groups was employed, which allowed a simple and cost-effective global deprotection step. The immunomodulatory properties of the synthesized multivalent mannosides were evaluated by assessing cytokine production in human white blood cell cultures. The Th2-type cytokines interleukin-4 and interleukin-5 (IL-4 and IL-5), the Th1 cytokine interferon-γ (IFN-γ), the Treg cytokine IL-10, and the pro-inflammatory cytokine tumor necrosis factor (TNF) were included in the screening. A single trivalent acetylated mannobiose derivative was identified as a potent inducer of Treg and Th1 immune response, resulting in strong IL-10 and moderate IFN-γ productions dose-dependently, while inducing no Th2 cytokine response. The immunomodulatory properties of this trivalent mannoside were further studied in vitro in allergen (Bet v)-stimulated human peripheral blood mononuclear cell cultures of birch pollen allergic subjects. Stimulation with birch pollen induced strong IL-4 and IL-5 responses, which could be suppressed by the trivalent acetylated mannobiose derivative. The IL-10 response was also suppressed, whereas the production of IFN-γ was strongly enhanced. The results suggest that the identified lead compound has suppressive effects on the Th2-type allergic inflammatory response and shows potential as a possible lead adjuvant for the specific immunotherapy of allergies. Copyright

MULTIVALENT [BETA] - 1 - 2 - LINKED MANNOSE OLIGOSACCHARIDES AS IMMUNOSTIMULATORY COMPOUNDS AND USES THEREOF

This invention relates to synthetic oligo- or multivalent beta- 1 - 2 - linked mannooligosaccharide compounds and to their use for modulating T helper (Th) and T regulatory (Treg) cell -mediated immune responses.

Synthesis of Cryptococcus neoformans Capsular Polysaccharide Structures. IV. Construction of Thioglycoside Donor Blocks and their Subsequent Assembly

Di- and trisaccharide thioglycoside building blocks, ethyl (2,3,4-tri-O-benzyl-β-D-xylopyranosyl)-(1 → 2)-3-O-allyl-4,6-di-O- benzyl-1-thio-α-D-mannopyranoside, ethyl (2,3,4-tri-O-benzyl-β-D- xylopyranosyl)-(1 → 2)-6-O-acetyl-3-O-allyl-4-O-benzyl-1-thio-α