41545-34-0

Upstream product

• 75-52-5 nitromethane 
• 23558-05-6 3-O-benzyl-1,2-O-isopropylidene-1,5-D-xylo-dialdofuranose 
• 350255-13-9 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose 
• 100-39-0 benzyl bromide 
• 908142-25-6 1-2 O-isopropylidene 3-O-benzyl α(D)gluco-pentoaldofuranose 
• 110316-24-0 3-O-benzyl-1,2-O-isopropylidene-β-D-arabino-pentodialdo-1,4-furanose 
• 563-70-2 bromonitromethane 
• 5447-97-2 2-bromo-2-nitropropane 
• 134275-39-1 3-O-benzyl-1,2-O-isopropylidene-β-D-altrofuranose 

Downstream Products

• 86495-59-2 (E)-3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-xylo-hex-5-eno-1,4-furanose 
• 99784-40-4 (4R)-4-(benzyloxy)-2-cyclopentenone 
• 99784-39-1 (3R,4R)-3-Benzyloxy-4-hydroxy-cyclopentanone 
• 69177-83-9 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-xylo-hex-5-enofuranose 
• 23312-95-0 5-[2-(amino)propan-2-yl]-3-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose 
• 1197893-86-9 3-((1R)-1-((3aR,5R,6S,6aR)-6-(benzyloxy)-tetrahydro-2,2-dimethylfuro[3,2-d][1,3]dioxol-5-yl)-2-nitroethyl)-2-methyl-1H-indole 
• 141782-01-6 (3aS,5R,6R,6aS)-6-Benzyloxy-2,2-dimethyl-5-((E)-2-nitro-vinyl)-tetrahydro-furo[2,3-d][1,3]dioxole 
• 551960-80-6 6-deoxy-6-N-benzyloxycarbonyl-1,2-O-isopropylidene-3-O-phenylmethyl-β-L-ido-1,4-furanose 
• 16647-61-3 1,6-dideoxy-1,6-imino-(2S,3R,4R,5S)-L-iditol 

Relevant academic research and scientific papers

Polymeric nanoassembly of imine functionalized magnetite for loading copper salts to catalyze Henry and A3-coupling reactions

Poly(ethylenimine) was grafted on the magnetite (Fe3O4) nanoparticles, and subsequently reacted with different aldehydes to form the imine functionalities (Fe3O4-Imine NPs). Thus formed Fe3O4/su

Solvent and catalyst free route to 3-indolyl glycoconjugates: Synthesis of sugar tethered isoxazolines and isoxazoles from 3-indolyl nitroalkanes

An expedient, solvent and catalyst free strategy for the synthesis of sugar based bis(indolyl)methanes and indolyl nitroalkanes has been developed. The protocol works well within a wide range of substrates, and tolerates various N/O protecting groups. The

Indium-mediated debromination of gem -bromonitroalkanes under mild conditions in aqueous medium

gem-Bromonitroalkanes are efficiently reduced into the corresponding dehalogenated products in excellent yields with indium metal in the presence of a palladium(0) catalyst and indium(III) chloride in aqueous medium. The addition of bromonitromethane to c

One-pot synthesis of vicinal aminoalkanols from sugar aldehydes

A novel synthetic method of carbohydrate derived vicinal aminoalcohols, from sugar aldehydes and bromonitroalkanes, has been developed. It involves an indium-catalyzed one-pot Henry reaction and nitro group reduction, and proceeds with a remarkably high anti-selectivity. The reaction of the intermediate aminoalcohols with alkylating agents furnished the corresponding carbohydrate-based tertiary aminoalcohols with excellent stereoselectivity. This very simple methodology allows easy access to families of N,N-dialkylated vicinal aminoalkanols, useful intermediates in the synthesis of derivatives of biological interest and sugar-based stereodifferentiating agents for asymmetric catalysis.

Synthesis of sugar-derived 2-nitroalkanols via Henry reaction promoted by samarium diiodide or indium

We present herein an improved synthesis of nitro sugars, consisting of a Henry-type reaction of bromonitromethane and sugar aldehydes. The reaction can be promoted by either SmI2 or indium metal, yielding in both cases high yields and good diastereoisomeric ratios. However, while the SmI 2-promoted reaction is very sensitive to steric factors and only gives satisfactory results with bromonitromethane, the indium-mediated reaction is not subjected to this limitation, giving excellent results with bromonitromethane as well as more hindered bromonitroalkanes. Georg Thieme Verlag Stuttgart New York.

Glycosynthase-Mediated Assembly of Xylanase Substrates and Inhibitors

An exo-β-xylosidase mutant with glycosynthase activity was created to aid in the synthesis of xylanase substrates and inhibitors. Simple monosaccharides were easily elaborated into di-, tri- and tetrasaccharides by using this enzyme. Some products proved

Indium-mediated reaction of 1-bromo-1-nitroalkanes with aldehydes: Access to 2-nitroalkan-1-ols

A novel method for the preparation of 2-nitroalkan-1-ols by an indium-promoted reaction of bromonitromethane with a variety of aldehydes is reported. The reaction was also performed with 2-bromo-2-nitropropanes to afford 2,2-dialkyl-2-nitroalkan-1-ols. The use of chiral sugar-derived aldehydes furnished the corresponding 2-nitroalkan-1-ols with excellent stereoselectivity. The utility of the novel sugar-derived 2,2-dialkyl-2-nitroalkan-1-ols for the preparation of branched iminosugar derivatives was demonstrated by the preparation of a hydroxymethyl branched polyhydroxylated azepane.

Synthesis of densely functionalised C-glycosides by a tandem oxy Michael addition-Wittig olefination pathway

Wittig olefination of 5,6-dideoxy-5,6-anhydro-6-nitro-d-glucofuranose (5) triggered a concomitant cyclisation via oxy Michael addition of the C2-hydroxyl group resulting in the formation of C-vinyl glycosides with Z-olefinic geometry.

Short and efficient synthesis of (2S,3R,4R,5R) and (2S,3R,4R,5S)-tetrahydroxyazepanes via the Henry reaction

The Henry reaction with the easily available α-d-xylo-pentodialdose afforded a diastereomeric mixture of nitroaldoses with the α-d-gluco- and β-l-ido-configuration, respectively, in good yield. When n-BuLi was used as the base, the reaction afforded the α

Orientation of the Addition of Dimethyl Phosphonate to 5,6-Dideoxy-6-nitro-D-hex-5-enofuranoses

The addition of dimethyl phosphonate to six 5,6-dideoxy-6-nitro-D-hex-5-enofuranoses at 25 deg C in the presence of triethylamine preponderantly gave (5R)-adducts, whereas the same reaction at 100 deg C without a base yielded (5S)-adducts as the main products.