657395-08-9

Basic information

• Product Name: methyl [2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(2-O-benzoyl-3-O-benzyl-6-O-levulinyl-α-L-idopyranosyl)-(1->4)-2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside
• Synonyms: methyl [2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(2-O-benzoyl-3-O-benzyl-6-O-levulinyl-α-L-idopyranosyl)-(1->4)-2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside
• CAS NO: 657395-08-9
• Molecular Weight: 1389.48
• Mol File: 657395-08-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: methyl [2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(2-O-benzoyl-3-O-benzyl-6-O-levulinyl-α-L-idopyranosyl)-(1->4)-2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl [2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(2-O-benzoyl-3-O-benzyl-6-O-levulinyl-α-L-idopyranosyl)-(1->4)-2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside(657395-08-9)
• EPA Substance Registry System: methyl [2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(2-O-benzoyl-3-O-benzyl-6-O-levulinyl-α-L-idopyranosyl)-(1->4)-2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside(657395-08-9)

Safety Data

• Hazardous Substances Data: 657395-08-9(Hazardous Substances Data)

Upstream product

• 501088-17-1 methyl 2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-α-D-glucopyranoside 
• 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 

Downstream Products

• 657395-21-6 methyl [2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-(2-naphthylmethyl)-α-D-glucopyranosyl]-(1->4)-(2-O-benzoyl-3-O-benzyl-α-L-idopyranosyl)-(1->4)-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.

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.