213598-45-9

Basic information

• Product Name: (3aR,6aS)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-N-oxide
• Synonyms: (3aR,6aS)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-N-oxide
• CAS NO: 213598-45-9
• Molecular Formula: C₇H₁₁NO₃
• Molecular Weight: 157
• EINECS: -0
• Mol File: 213598-45-9.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3aR,6aS)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-N-oxide(CAS DataBase Reference)
• NIST Chemistry Reference: (3aR,6aS)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-N-oxide(213598-45-9)
• EPA Substance Registry System: (3aR,6aS)-2,2-dimethyl-4,6a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyrrole-N-oxide(213598-45-9)

Safety Data

• Hazardous Substances Data: 213598-45-9(Hazardous Substances Data)

Upstream product

• 223396-44-9 meso 3,4-cis-isopropylidenedioxy-1-hydroxypyrrolidine 
• 2873-29-2 D-glucal triacetate 
• 189996-60-9 2,3-O-isopropylidene-D-erythrose 
• 63952-83-0 (2S)-acetic acid 6-oxo-3,6-dihydro-2H-pyran-2-ylmethyl ester 
• 849480-74-6 (E/Z)-2,3-O-ispropylidene-D-erythrose-oxime 
• 55904-12-6 ((4R,5S)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-methanol 
• 38279-61-7 meso-2,3-O-isopropylidene-1,4-di-O-(methanesulfonyl)butane-1,2,3,4-tetrol 
• 151948-15-1 (3aR,6aS)-5-benzyl-2,2-dimethyltetrahydro-3aH-[1,3]dioxolo[4,5-c]pyrrole 
• 124-63-0 methanesulfonyl chloride 
• 33647-85-7 isolevoglucosenone 
• 152139-64-5 (meso)-3,4-isopropylidenedioxy-2,5-pyrrolidine hydrotosylate 

Downstream Products

• 1219497-32-1 (2R,3S,4R)-2-phenylsulfonylmethyl-1-hydroxy-3,4-isopropylidenedioxypyrrolidine 
• 1369963-65-4 (3R,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole 
• 1369963-66-5 (3S,3aR,4S,5R)-3-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole 
• 1369963-68-7 (2S,3aS,4S,5R)-2-phenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole 
• 1369963-67-6 (2R,3aS,4S,5R)-2-pchenylsulfonyl-4,5-isopropylidenedioxy-hexahydropyrrolo[1,2-b]isoxazole 
• 464-72-2 tetraphenylethane-1,2-diol 
• 1384970-76-6 (3aS,4R,6aR)-4-(hydroxydiphenylmethyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-ol 
• 223396-44-9 meso 3,4-cis-isopropylidenedioxy-1-hydroxypyrrolidine 
• 1636-34-6 2,3-diphenyl-2,3-butanediol 
• 1384970-69-7 (3aS,4R,6aR)-4-[(R)-1-hydroxy-1-phenylethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-ol 
• 1384970-68-6 (3aS,4R,6aR)-4-[(S)-1-hydroxy-1-phenylethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-ol 
• 1384970-74-4 (3aS,4R,6aR)-4-[(S)-1-(4-(dimethylamino)phenyl)-1-hydroxyethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-ol 
• 114890-27-6 2,3-bis-(4-dimethylamino-phenyl)-butane-2,3-diol 
• 1384970-71-1 (3aS,4R,6aR)-4-[(R)-1-hydroxy-1-(4-methoxyphenyl)ethyl]-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyrrol-5-ol 

Relevant articles and documents

Oxidation of hydroxylamines to nitrones catalyzed by (salen)Mn(III) complexes. Enantioselective synthesis of a protected cis-dihydroxypyrroline N-oxide with Jacobsen catalyst

Oxidation of N,N-disubstituted hydroxylamines to nitrones catalyzed by the Jacobsen catalyst occurs cleanly in the presence of hydrogen peroxide, sodium hypochlorite or iodosylbenzene as the stoichiometric oxidant. Meso 3,4-cis-isopropylidenedioxy-1-hydro

Straightforward synthesis of enantiomerically pure (3S,4R)- and (3R,4S)-3,4-isopropylidenedioxypyrroline 1-oxide, precursors of functionalized cis-dihydroxy azaheterocycles, by a novel "one-pot" procedure

The enantiomerically pure nitrone 3, a valuable precursor of mono- and bicyclic azaheterocycles, has been synthesized in 57% yield by a novel "one-pot" process starting from lactol 1, in turn readily available from Darabinose. The same process, consisting

Synthesis of a new chiral pyrrolidine

The synthesis of a new chiral pyrrolidine has been performed using 2,3-O-isopropylidene-D-erythronolactol as a suitable starting material.

Kinetic and thermodynamic aspects in the 1,3-dipolar cycloaddition of five-membered cyclic nitrones to α,β-unsaturated γ- and δ-lactones

The 1,3-dipolar cycloaddition of five-membered ring nitrones to the α,β-unsaturated δ-lactones is kinetically controlled, whereas the same reactions involving γ-lactones, upon heating and prolonged reaction times, display visible reversibility of the reac

One-pot synthesis of cyclic nitrones and their conversion to pyrrolizidines: 7a-epi-crotanecine inhibits α-mannosidases

A new straightforward and inexpensive one-pot procedure is described for the preparation of enantiopure five-membered cyclic nitrones starting from the corresponding lactols. Its efficiency relies on the condensation of unprotected hydroxylamine with read

Nitrone cycloadditions to isolevoglucosenone: Ready access to a new class of directly linked (1→3)-imino-C-disaccharides

(Matrix presented) Straightforward access to a new class of D-gulo- and D-allo-derived directly linked (1→3)-imino-C-disaccharides by means of cycloaddition reactions of enantiopure polyhydroxylated pyrroline N-oxides with isolevoglucosenone is reported. The cycloaddition reactions display a high level of double asymmetric induction, which allows a partial kinetic resolution of a racemic nitrone.

TBAT-mediated nitrone formation of ω-mesyloxy-O-tert-butyldiphenylsilyloximes: Facile synthesis of cyclic nitrones from hemiacetals

Chiral and cyclic nitrones were synthesized by TBAT-mediated desilylative cyclization of ω-mesyloxy-O-tert-butyl-diphenylsilyloximes, readily prepared from sugar derivatives by a consecutive treatment with O-tert-butyldiphenylsilylhydroxylamine and with m

Manganese dioxide oxidation of hydroxylamines to nitrones

Several structurally differentiated N,N-dialkylhydroxylamines were oxidised to the corresponding nitrones using MnO2. Manganese dioxide revealed an efficient and mild reagent for oxidation of hydroxylamines, showing a level of regioselectivity

Complete stereoselective synthesis of quasi-enantiomeric pseudo imino-C- disaccharides: Parallel kinetic resolution of a racemic cis- dihydroxypyrroline N-oxide by 1,2-glycals

Cycloadditions of hydroxylated enantiopure pyrroline N-oxides to 1,2- glycals display high double-asymmetric induction. The selectivity is controlled by the stereochemistry at C-3 of the glycal. A parallel kinetic resolution experiment with a racemic cis-dihydroxypyrroline N-oxide allowed the synthesis of two different pseudo imino-C-disaccharides precursors in a completely enantiopure form, totally avoiding the formation of minor cycloadducts.