213617-02-8

Upstream product

• 213617-00-6 2,3,5-tri-O-benzyl-D-ribose oxime 
• 16838-89-4 2,3,5-tri-O-benzyl-D-ribofuranose 
• 213617-01-7 C₄₂H₄₆INO₄Si 

Downstream Products

• 1454681-25-4 (2R,3R,5R,6R,7S,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-2-ol 
• 1454681-24-3 (2S,3S,5R,6R,7S,7aS)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-3-methylhexahydro-1H-pyrrolizin-2-ol 
• 1454681-14-1 1-[((2S, 3aS, 4S, 5R, 6R)-4,5-bis(benzyloxy)-6-benzyloxymethyl)hexahydropyrrolo[1,2-b]isoxazol-2-yl]ethanone 
• 1361226-72-3 (1S,2R,3R,6S,7aS)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-1H-pyrrolizine 
• 1361226-70-1 (1S,2R,3R,6S,7aS)-1,2-bis(benzyloxy)-3-[(benzyloxy)methyl]-6-hydroxyhexahydro-5H-pyrrolizin-5-one 
• 1361226-71-2 C₃₁H₃₃NO₆ 
• 1361226-83-6 (1S,2R,3R,6S,7aS)-1,2-bis-benzyloxy-3-benzyloxymethyl-6-metansulfonyloxyhexahydro-5H-pyrrolizin-5-one 

Relevant academic research and scientific papers

Gold Supported on Silica Catalyzes the Aerobic Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones

A new method for the preparation of nitrones through the aerobic oxidation of the corresponding N,N-disubstituted hydroxylamines has been developed by exploring a new catalytic reactivity of gold supported on silica. The oxidation occurs under very mild c

Diruthenium Diacetate Catalysed Aerobic Oxidation of Hydroxylamines and Improved Chemoselectivity by Immobilisation to Lysozyme

A new green method for the preparation of nitrones through the aerobic oxidation of the corresponding N,N-disubstituted hydroxylamines has been developed upon exploring the catalytic activity of a diruthenium catalyst, that is, [Ru2(OAc)4Cl]), in aqueous or alcoholic solution under mild reaction conditions (0.1 to 1 mol % catalyst, air, 50 °C) and reasonable reaction times. Notably, the catalytic activity of the dimetallic centre is retained after its binding to the small protein lysozyme. Interestingly, this new artificial metalloenzyme conferred complete chemoselectivity to the oxidation of cyclic hydroxylamines, in contrast to the diruthenium catalyst.

On the Oxidation of Hydroxylamines with o -Iodoxybenzoic Acid (IBX)

o -Iodoxybenzoic acid (IBX) is confirmed as a powerful tool for the oxidation of hydroxylamines. The synthetic route is demonstrated as efficient and user friendly, and is exploited on various carbohydrate-derived N,N-disubstituted hydroxylamines (cyclic, acyclic, and functionalized ones), affording the corresponding nitrones in good yields and regioselectivity. N-Monosubstituted hydroxylamines revealed an interesting divergent behavior depending on the reaction conditions. While IBX oxidation in dimethyl sulfoxide at 45 °C furnished oximes as reported, the oxidation in dichloromethane at room temperature afforded efficiently the unusual corresponding nitroso dimers.

Oxidation of N,N-Disubstituted Hydroxylamines to Nitrones with Hypervalent Iodine Reagents

Hypervalent iodine compounds are viable reagents for the oxidation of N,N-disubstituted hydroxylamines to the corresponding nitrones, with IBX performing best. The procedure is very simple and user-friendly and affords the target compounds with high effic

A convenient approach toward the synthesis of enantiopure isomers of DMDP and ADMDP

A practical method for the synthesis of five-membered iminocyclitols, pyrrolidine alkaloids bearing multiple hydroxyl substituents, has been developed. All of the eight key intermediates, enantiopure tri-O-benzyl cyclic nitrones, are prepared from four cheap, readily available d-aldopentoses. The nucleophilic addition of cyclic nitrones with vinyl magnesium chloride and TMSCN shows high 2,3-trans stereoselectivity. To construct the 2,3-cis configurations, inversion of the C-2 nitrile group is achieved via an elimination-reduction sequence. Using this approach, five isomers of DMDP and six isomers of ADMDP are prepared efficiently. In the biological evaluation, iminocyclitol 27 is a new and potent inhibitor against β-hexosaminidase with an IC50 value of 0.2 μM.

Synthesis and reactions of chiral cyclic nitrones derived from D-ribose

A facile route to chiral cyclic nitrones derived from D-ribose is described. Their versatility as substrates for 1,3-dipolar cycloadditions and nucleophilic additions is demonstrated.