657394-99-5

Upstream product

• 93-97-0 benzoic acid anhydride 
• 1253948-04-7 2-azido-2-deoxy-1,3,4,6-tetra-O-trimethylsilyl-D-glucopyranose 
• 66-99-9 β-naphthaldehyde 
• 54769-36-7 N-benzoyloxybenzotriazole 
• 100-39-0 benzyl bromide 
• 923952-61-8 2-azido-2-deoxy-4,6-O-(2-naphthylmethylidene)-β-D-glucopyranosyl benzoate 

Downstream Products

• 1355357-16-2 methyl 2-azido-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside 
• 1355357-15-1 methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranoside 
• 882689-13-6 C₃₃H₂₉Cl₃N₄O₆ 
• 175978-55-9 methyl 2-azido-3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 501088-17-1 methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 657395-04-5 C₇₄H₇₂N₆O₁₈ 
• 657395-06-7 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl levulinate 
• 657395-07-8 4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphth-ylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-levulinyl-L-idopyranosyl trichloroacetimidate 
• 657395-03-4 C₅₅H₅₁Cl₃N₄O₁₃ 
• 657395-02-3 6-O-acetyl-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-L-idopyranosyl acetate 
• 657395-01-2 1,6-anhydro-4-O-[2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-β-L-idopyranose 
• 657395-19-2 Benzoic acid (2R,3S,4R,5R)-5-azido-4-benzyloxy-3-(naphthalen-2-ylmethoxy)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-2-ylmethyl ester 
• 657395-16-9 C₃₈H₃₃N₃O₇ 
• 657395-15-8 2-azido-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-β-D-glucopyranosyl benzoate 

Relevant academic research and scientific papers

Synthesis of heparin oligosaccharides and their interaction with eosinophil-derived neurotoxin

A convenient route for the synthesis of heparin oligosaccharides involving regioselective protection of d-glucosamine and a concise preparation of rare l-ido sugars from diacetone α-d-glucose is described. Stereoselective coupling of a d-glucosamine-derived trichloroacetimidate with a 1,6-anhydro-β-l-idopyranosyl 4-alcohol gave the desired α-linked disaccharide, which was used as repeating unit for dual chain elongation and termination. Stepwise assembly from the reducing to the non-reducing end with a d-glucosamine-derived monosaccharide as starting unit furnished the oligosaccharide skeletons having different chain lengths. A series of functional group transformations afforded the expected heparin oligosaccharides with 3, 5 and 7 sugar units. Interaction of these oligosaccharides with eosinophil-derived neurotoxin (EDN), a cationic ribonuclease and a mediator produced by human eosinophils, was further investigated. The results revealed that at 5 μg mL-1, the heptasaccharide has sufficiently strong interference to block EDN binding to Beas-2B cells. The tri- and pentasaccharides have moderate inhibitory properties at 50 μg mL-1 concentration, but no inhibition has been observed at 10 μg mL-1. The IC50 values of the tri-, penta- and heptasaccharides are 69.4, 47.2 and 0.225 μg mL-1, respectively.

DISACCHARIDE COMPOUNDS

Disaccharide compounds used as building blocks for making heparin and heparan sulfate oligosaccharides. Also disclosed are methods for making these disaccharide compounds.

Synthesis of 48 disaccharide building blocks for the assembly of a heparin and heparan sulfate oligosaccharide library

(Chemical Equation Presented) An efficient synthesis of the entire set of suitably protected 48 disaccharide building blocks for the assembly of a heparin and heparan sulfate oligosaccharide library is described here.

Synthesis of Heparin Oligosaccharides

An efficient preparation of rare 2-O-benzoyl-3-O-benzyl-1,6-anhydro-β-l-idopyranose from commercially available diacetone α-d-glucose in five straightforward steps is described here. With this key building block in hand, the total syntheses of heparin oligosaccharides with three, five, seven, and nine sugar units are successfully carried out. Copyright

Biologically potent L-hexoses and 6-deoxy-L-hexoses: Their syntheses and applications

This account describes our recent work in the development of new methodologies to prepare rare and biologically potent L-hexoses and 6-deoxy-L-hexoses, from cheapest D-glucose, via L-hexofuranoses and 1,6-anhydro-β-L-hexopyranoses as key building blocks. Their applications in the syntheses of heparin oligosaccharides, the carbohydrate moiety of bleomycin A2, and L-acovenose are also summarized here.