Increased formation of oxepanes in non-aqueous medium in the cycloaddition of 3-O-allyl-1,2-isopropylidenefuranose N-Ph nitrones

Datta, Shreyasi; Nath, Madhumita; Chowdhury, Sandip; Bhattacharjya, Anup

doi:10.1016/j.tetlet.2008.03.014

Cited by 7 publications

(2 citation statements)

References 9 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…As a consequence, reports of nitrone cycloaddition continue to emerge in the literature using carbohydrates as a precursor, Shing et al (24) reported stereo-and regioselectivity in intramolecular nitrone-alkene cycloaddition of hept-6-enose derived from carbohydrates. Torrente (22,25,26) and Datta et al reported the formation of oxepanes from intramolecular 1,3-dipolar cycloaddition of D-glucose-derived nitrone (27). Coskun et al (28,29) reported dipolar cycloaddition of nitrone with N-arylmaleimides, which can be cited as example for 1,3 dipolar cycloaddition of nitrone with cyclic dienophiles.…”

mentioning

confidence: 99%

“…Isoxazolidines derived from carbohydrate based nitrones are potential intermediates for the synthesis of various aza sugars, on account of the presence of amino group in the masked form (19)(20)(21)(22)(23). Torrente et al, Karanjule et al and Jachak et al developed inter-and intramolecular 1,3-dipolar cycloaddition reactions of D-glucose-derived nitrone (22,25,26) and Datta et al reported the formation of oxepanes from intramolecular 1,3-dipolar cycloaddition of D-glucose-derived nitrone (27). Torrente et al, Karanjule et al and Jachak et al developed inter-and intramolecular 1,3-dipolar cycloaddition reactions of D-glucose-derived nitrone (22,25,26) and Datta et al reported the formation of oxepanes from intramolecular 1,3-dipolar cycloaddition of D-glucose-derived nitrone (27).…”

mentioning

confidence: 99%

See 1 more Smart Citation

Antibacterial Activity, Quantitative Structure–Activity Relationship and Diastereoselective Synthesis of Isoxazolidine Derivatives Via 1,3‐Dipolar Cycloaddition of d‐glucose Derived Nitrone with Olefin

et al. 2009

View full text Add to dashboard Cite

The diastereoselectivity of the intermolecular 1,3-dipolar cycloaddition reaction of d-glucose-derived nitrones with both cyclic and acyclic dipolarophiles were studied. The reaction of nitrone with acyclic dipolarophiles resulted in the formation of the endo adduct exclusively whereas with cyclic dipolarophiles endo adduct was obtained as the major product. Antibacterial activity was evaluated for these eighteen isoxazolidine derivatives against Staphylococcus aureus NCIM5021, Escherichia coli NCIM 2931 and Pseudomonas aeruginosa NCIM 5029 by twofold dilution technique using resazurin as the indicator dye. Quantitative structureactivity relationships were developed with fourteen and the model was validated with four data. Electronic and spatial descriptors were the major contributors in all the three quantitative structureactivity relationship equations and the statistical parameters r(2), r(2)(adj) , F-ratio and q(2) were found to be satisfactory.

show abstract

mentioning

confidence: 99%

mentioning

confidence: 99%

Antibacterial Activity, Quantitative Structure–Activity Relationship and Diastereoselective Synthesis of Isoxazolidine Derivatives Via 1,3‐Dipolar Cycloaddition of d‐glucose Derived Nitrone with Olefin

et al. 2009

View full text Add to dashboard Cite

show abstract

Epimerization of the α Stereocenter in d‐Ribose‐Derived Nitrones: Direct Access to Variant Quinolizidines with d‐Ribo and d‐Arabino Configurations

et al. 2015

View full text Add to dashboard Cite

The concise synthesis of two polyhydroxyquinolizidines from 2,3-O-isopropylidene-d-ribofuranose was accomplished. Epimerization of the intermediate N-(3-alkenyl)nitrone resulted in exceptionally straightforward access to an iminosugar with a d-arabino configuration. A plausible mechanism of the epimerization via nitrone-enehydroxylamine tautomerism explaining the reaction course has been proposed.

show abstract

ChemInform Abstract: Increased Formation of Oxepanes in Non‐aqueous Medium in the Cycloaddition of 3‐O‐Allyl‐1,2‐isopropylidenefuranose N‐Ph Nitrones.

et al. 2008

View full text Add to dashboard Cite

It is demonstrated that the N-phenyl nitrones derived from carbohydrates (Ia)-(Id) undergo improved intramolecular 1,3-dipolar cycloaddition compared to the previously reported N-Me or N-Bn nitrones. Oxepane products are obtained in better yields or together with the pyran skeletons [cf. (V)]. In the case of (Ie), only the pyran is formed in analogy to the N-Me analogue. -(DATTA, S.; NATH, M.; CHOWDHURY, S.; BHATTACHARJYA*, A.; Tetrahedron Lett. 49 (2008) 18, 2935-2938; Dep. Chem., Indian Inst. Chem. Biol., Kolkata 700 032, India; Eng.) -Lindner 33-173

show abstract

Increased formation of oxepanes in non-aqueous medium in the cycloaddition of 3-O-allyl-1,2-isopropylidenefuranose N-Ph nitrones

Cited by 7 publications

References 9 publications

Antibacterial Activity, Quantitative Structure–Activity Relationship and Diastereoselective Synthesis of Isoxazolidine Derivatives Via 1,3‐Dipolar Cycloaddition of d‐glucose Derived Nitrone with Olefin

Antibacterial Activity, Quantitative Structure–Activity Relationship and Diastereoselective Synthesis of Isoxazolidine Derivatives Via 1,3‐Dipolar Cycloaddition of d‐glucose Derived Nitrone with Olefin

Epimerization of the α Stereocenter in d‐Ribose‐Derived Nitrones: Direct Access to Variant Quinolizidines with d‐Ribo and d‐Arabino Configurations

ChemInform Abstract: Increased Formation of Oxepanes in Non‐aqueous Medium in the Cycloaddition of 3‐O‐Allyl‐1,2‐isopropylidenefuranose N‐Ph Nitrones.

Contact Info

Product

Resources

About