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

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

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.

Nickel-catalyzed stereoselective formation of α-2-deoxy-2-amino glycosides

(Chemical Equation Presented) The development of a new method for the stereoselective synthesis of α-2-deoxy-2-amino glycosides is described. This methodology relies on the nature of the cationic nickel catalyst, generated in situ from LnNiCl2 and AgOTf, to direct the anomeric stereoselectivity. The new glycosylation reaction is highly α-selective and proceeds under mild conditions with 5-10 mol % of the nickel catalyst loading at ambient temperature. This new method has been applied to both D-glucosamine and galactosamine trichloroacetimidate donors as well as an array of primary, secondary, and tertiary alcohol nucleophiles to provide the desired glycoconjugates in good yields with excellent α-selectivity. Mechanistic studies of the present reaction are underway and will be reported in due course. Copyright

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