146815-14-7

Basic information

• Product Name: 2-Phenyl-3-(1,2-O-isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-5-(2,6-dimethylphenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole
• CAS NO: 146815-14-7
• Molecular Weight: 522.555
• Mol File: 146815-14-7.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 2-Phenyl-3-(1,2-O-isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-5-(2,6-dimethylphenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Phenyl-3-(1,2-O-isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-5-(2,6-dimethylphenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole(146815-14-7)
• EPA Substance Registry System: 2-Phenyl-3-(1,2-O-isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-5-(2,6-dimethylphenyl)-4,6-dioxo-2,3,3a,4,6,6a-hexahydropyrrolo<3,4-d>isoxazole(146815-14-7)

Safety Data

• Hazardous Substances Data: 146815-14-7(Hazardous Substances Data)

Upstream product

• 1206-49-1 N-(2,6-dimethylphenyl)maleimide 
• 146814-99-5 C-(1,2-O-Isopropylidene-3-acetoxy-α-D-xylo-tetrofuranos-4-yl)-N-phenylnitrone 
• 100-65-2 N-Phenylhydroxylamine 
• 24807-97-4 3-O-acetyl-1,2-O-isopropylidene-α-D-xylo-pentodialdo-1,4-furanose 

Relevant articles and documents

Preparation and Stereoselectivity of 1,3-Dipolar Cycloaddition of C-Glycosyl Nitrones to N-Arylmaleimides

The cycloaddition of 3'-hydroxyglycosyl-N-methylnitrone (1) to N-arylmaleimides gave the syn isoxazolidines 6, whereas 3'-acetoxyglycosyl-N-methylnitrone (2) afforded the anti isoxazolidines 8 and 10.The formation of 6 was rationalized by an exo attack, stereoelectronically preferred through the hydrogen bond between the pentose hydroxyl group and one of the carbonyl groups of N-arylmaleimide.The sterically preferred endo attack avoiding the repulsions between N-arylmaleimide and sugar moiety was proposed for addition of 2.The structure and steric configuration of the products have been assigned on the basis of 1H- and 13C-NMR spectroscopy, mainly by nuclear Overhauser effect difference spectroscopy.AM1 calculations of the nitrones and MM2 calculations of the adducts were performed. Keywords: 1,3-Dipolar cycloaddition of chiral nitrones; 3'-Hydroxy- and 3'-acetoxyglycosyl-N-methylnitrones; Stereoselectivity of 1,3-dipolar cycloaddition; AM1 calculations.