130005-73-1

Basic information

• Product Name: 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranose
• CAS NO: 130005-73-1
• Molecular Weight: 423.42
• Mol File: 130005-73-1.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranose(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranose(130005-73-1)
• EPA Substance Registry System: 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-β-D-glucopyranose(130005-73-1)

Safety Data

• Hazardous Substances Data: 130005-73-1(Hazardous Substances Data)

Upstream product

• 61567-93-9 3,4,6-tri-O-acetyl-2-deoxy-2-(4-methoxybenzyl)imino-α-D-glucopyranosyl bromide 
• 51471-40-0 6-(hydroxymethyl)-3-[4-methoxybenzylideneamino]tetrahydropyran-2,4,5-triol 
• 108-24-7 acetic anhydride 
• 14131-63-6 D-glucosamine hydrochloride 
• 123-11-5 4-methoxy-benzaldehyde 
• 114297-26-6 1,3,4,6-tetra-O-acetyl-2-deoxy-2-{[(4-methoxyphenyl)methylidene]amino}-D-glucopyranose 
• 7597-81-1 1,3,4,6-tetra-O-acetyl-2-deoxy-2-(4-methoxybenzylidene)amino-β-D-glucopyranose 

Downstream Products

• 129729-41-5 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-α-D-glucopyranosyl trichloroacetimidate 
• 1203584-55-7 tert-butyldiphenylsilyl 3,4,6-tri-O-benzyl-2-deoxy-2-(4-methoxybenzylideneamino)-β-D-glucopyranose 
• 1203584-64-8 tert-butyldiphenylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranose 
• 1203584-66-0 3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranosyl N-(phenyl)trifluoroacetimidate 
• 1203584-65-9 tert-butyldiphenylsilyl 3,4,6-tri-O-benzyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranose 
• 1203584-67-1 3,4,6-tri-O-benzyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-D-glucopyranosyl N-(phenyl)trifluoroacetimidate 
• 1203584-56-8 methyl 3,4,6-tri-O-acetyl-2-deoxy-2-(4-nitrobenzenesulfonylamino)-β-D-glucopyranoside 
• 1203584-68-2 tert-butyldiphenylsilyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-D-glucopyranose 
• 1082706-19-1 C₁₈H₂₁N₃O₁₂ 
• 1203584-70-6 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-D-glucopyranosyl N-(phenyl)trifluoroacetimidate 
• 1203584-69-3 tert-butyldiphenylsilyl 3,4,6-tri-O-benzyl-2-deoxy-2-(2,4-dinitrophenylamino)-β-D-glucopyranose 
• 1203584-59-1 C₄₆H₅₁N₃O₁₇ 
• 1203584-61-5 iso-propyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,4-dinitrophenylamino)-α-D-glucopyranosyl-(1->4)-(methyl 3-O-benzyl-2-O-pivaloyl-α-L-idopyranosyluronate) 
• 1203584-54-6 1-O-tert-butyldiphenylsilyl-3,4,6-tri-O-acetyl-2-deoxy-2-amino-β-D-glucopyranoside 

Relevant articles and documents

2-Isocyano glucose used in Ugi four-component reaction: An approach to enhance inhibitory effect against DNA oxidation

The Ugi four-component-reaction (Ugi 4CR) allowed synthesizing bisamide from carboxylic acid, aldehyde, amine, and isocyanide in one-pot operation. However, introducing 2-isocyano glucose into the Ugi 4CR and investigating the inhibitory effects of Ugi adducts against radical-induced oxidation of DNA remained technical challenges. We herein applied 2-isocyano glucose (acetylation of hydroxy groups) to perform a catalyst-free Ugi 4CR at room temperature. The gallic, ferulic, caffeic, or p-hydroxybenzoic acids, aniline (or benzylamine and p-aminophenol), and formaldehyde acted as reagents. In the case of inhibiting DNA oxidations induced by 2,2’-azobis(2-amidinopropane hydrochloride) (AAPH), hydroxy radical, and Cu2+/glutathione, the Ugi adduct containing glucose moiety exhibited higher antioxidative activities than the structural analog without glucose moiety involved. It was also proved that high antioxidative property was owing to hydroxy groups in glucose moiety. Therefore, sugar-appended Ugi adducts might hold promising inhibitors for DNA oxidation.

Synthesis of differentially protected glucosamine building blocks and their evaluation as glycosylating agents

The modular assembly of heparin oligosaccharides requires glucosamine building blocks with amine protecting groups for α-selective glycosylations that can be readily removed. The synthesis of N-4-nitrobenzensulphonamide (nosyl)- and N-2,4-dinitrophenyl (DNP)-protected glucosamine building blocks and their evaluation as glycosylating agents is described. The N-nosyl-protected glucosamine building blocks were challenging to prepare and their glycosylations resulted in inseparable mixtures of products. The N-DNP-protected glucosamines, however, were readily synthesized and resulted in α-selective couplings to protected l-iduronic acid derivatives.

N-p-methoxybenzylidene derivatives of 2-amino-2-deoxy-D-glucose as glycosyl donors: a reinvestigation.

6-O-Acetyl-3,4-di-O-benzyl-2-deoxy-2-p-methoxybenzylideneamino-D- glucopyranosyl chloride, 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-alpha-D-glu copyranosyl bromide, 3,4,6-tri-O-acetyl-2-deoxy-2-p-methoxybenzylideneamino-alpha- and -beta-D- g