657394-99-5

Basic information

• Product Name: 2-azido-3-O-benzyl-2-deoxy-4,6-O-(2-naphthylmethylidene)-β-D-glucopyranosyl benzoate
• Synonyms: 2-azido-3-O-benzyl-2-deoxy-4,6-O-(2-naphthylmethylidene)-β-D-glucopyranosyl benzoate
• CAS NO: 657394-99-5
• Molecular Weight: 537.572
• Mol File: 657394-99-5.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 2-azido-3-O-benzyl-2-deoxy-4,6-O-(2-naphthylmethylidene)-β-D-glucopyranosyl benzoate(CAS DataBase Reference)
• NIST Chemistry Reference: 2-azido-3-O-benzyl-2-deoxy-4,6-O-(2-naphthylmethylidene)-β-D-glucopyranosyl benzoate(657394-99-5)
• EPA Substance Registry System: 2-azido-3-O-benzyl-2-deoxy-4,6-O-(2-naphthylmethylidene)-β-D-glucopyranosyl benzoate(657394-99-5)

Safety Data

• Hazardous Substances Data: 657394-99-5(Hazardous Substances Data)

Upstream product

• 93-97-0 benzoic acid anhydride 
• 66-99-9 β-naphthaldehyde 
• 1253948-04-7 2-azido-2-deoxy-1,3,4,6-tetra-O-trimethylsilyl-D-glucopyranose 
• 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

• 657395-15-8 2-azido-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-β-D-glucopyranosyl benzoate 
• 657395-16-9 C₃₈H₃₃N₃O₇ 
• 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 
• 657395-01-2 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 
• 657395-02-3 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 
• 657395-03-4 C₅₅H₅₁Cl₃N₄O₁₃ 
• 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 
• 657395-06-7 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 
• 657395-04-5 C₇₄H₇₂N₆O₁₈ 
• 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 

Relevant articles and documents

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.

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.

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.