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Volumn , Issue 5, 2008, Pages 687-690

Unexpected reactions: From (2S,3R)-2-(endo-D-galacto-pentaacetoxypentyl)-1, 4-dimethyl-3-exo-nitro-7-oxabicyclo[2.2.1]hept-5-ene to chiral cyclic ethers

Author keywords

Asymmetric synthesis; Carbohydrate nitroalkenes; Diels Alder reaction; Heterocycles; Ring opening

Indexed keywords

2 (ENDO DEXTRO GALACTO PENTAACETOXYPENTYL) 1,4 DIMETHYL 3 EXO NITRO 7 OXABICYCLO[2.2.1]HEPT 5 ENE; 2,5 DIMETHYLFURAN; BICYCLO COMPOUND; DEXTRO GALACTO 3,4,5,6,7 PENTA O ACETYL 1,2 DIDEOXY 1 NITROHEPT 1 ENITOL; ETHER DERIVATIVE; FURAN DERIVATIVE; NITRO DERIVATIVE; UNCLASSIFIED DRUG;

EID: 41349095728     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1042798     Document Type: Article
Times cited : (6)

References (28)
  • 9
    • 41349088792 scopus 로고    scopus 로고
    • 'Catalytic Asymmetric Diels-Alder Reactions': Hayashi, Y. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2001, 5.
    • (a) 'Catalytic Asymmetric Diels-Alder Reactions': Hayashi, Y. In Cycloaddition Reactions in Organic Synthesis; Kobayashi, S.; Jørgensen, K. A., Eds.; Wiley-VCH: Weinheim, 2001, 5.
  • 15
    • 41349088124 scopus 로고    scopus 로고
    • This ratio was determined from the 1H NMR spectra of the crude mixture at the end of reaction time, by integration of the signals corresponding to H-5 and H-6 of each stereoisomer
    • 1H NMR spectra of the crude mixture at the end of reaction time, by integration of the signals corresponding to H-5 and H-6 of each stereoisomer.
  • 18
    • 41349093318 scopus 로고    scopus 로고
    • The adduct 3 did not afford suitable crystals for their study by single-crystal X-ray analysis. Hence, this compound was analyzed using X-ray powder diffractometry to determine its crystalline structure. The powder was loaded into the holder (3 mm thick) and pressed slightly with a glass slide to ensure a flat surface and thus the absence of instrumental shift in the position of peaks in the diffractogram. The operating conditions for the data collection were: Cu Kα incident radiation (λ, 1.54183 Å, 5-70° scanning interval, 0.02° step size, and 40 s count time per step, using a Philips PW-1800 diffractometer equipped with a graphite secondary monochromator. The compound crystallized in the monoclinic system, with the space group C2, one molecule in the asymmetric unit giving four molecules in the unit cell (Z, 4, and the following unit cell dimensions: a, 23.8333 (10) Å, b, 10.0745 (4) Å, c, 14.3027 (6) A
    • The adduct 3 did not afford suitable crystals for their study by single-crystal X-ray analysis. Hence, this compound was analyzed using X-ray powder diffractometry to determine its crystalline structure. The powder was loaded into the holder (3 mm thick) and pressed slightly with a glass slide to ensure a flat surface and thus the absence of instrumental shift in the position of peaks in the diffractogram. The operating conditions for the data collection were: Cu Kα incident radiation (λ = 1.54183 Å), 5-70° scanning interval, 0.02° step size, and 40 s count time per step, using a Philips PW-1800 diffractometer equipped with a graphite secondary monochromator. The compound crystallized in the monoclinic system, with the space group C2, one molecule in the asymmetric unit giving four molecules in the unit cell (Z = 4), and the following unit cell dimensions: a = 23.8333 (10) Å, b = 10.0745 (4) Å, c = 14.3027 (6) Å, and β = 113.28 (1)°. As starting configuration was used the molecule optimized by molecular modelling with a semiempirical quantum chemistry model [code HyperChem: HYPERCHEM. Release 5. Standalone Version. Computational Chemistry, Hypercube Inc., Publication HC50-00-03-00, October 1996, ISBN 1-896164-17-X]. The structure was solved by direct-space methods with a 'Monte-Carlo/parallel tempering' search algorithm [code FOX: Favre-Nicolin, V.; Cern, R. FOX: a program for ab initio structure solution from powder diffraction data. Laboratory of Crystallography, University of Geneva, Switzerland, 2000], followed by a final refinement using the Rieltved method [code FullProf: Rodríguez-Carvajal, J. FULLPROF: a program for Rietveld refinement and pattern matching analysis. Abstracts of the Satellite Meeting on powder diffraction of the XV Congress of the International Union of Crystallography, Toulouse, France, 1990].
  • 23
    • 41349103835 scopus 로고    scopus 로고
    • +) resin.
    • +) resin.
  • 28
    • 41349108197 scopus 로고    scopus 로고
    • Selected Data for Compound 3 White solid; 43% yield; [α]D20 -27.2 (c 0.51, CHCl3, mp 189-190°C. 1H NMR (400 MHz, CDCl3, δ, 6.40 (d, 1 H, J5,6, 5.6 Hz, H-6, 6.24 (d, 1 H, H-5, 4.77 (dd, 1 H, J1′,2, 11.3 Hz, H-1′, 4.35 (d, 1 H, J2,3, 3.4 Hz, H-3, 2.97 (dd, 1 H, H-2, 13C NMR (100 MHz, CDCl3, δ, 143.1 (C-6, 136.6 (C-5, 92.8 (C-3, 88.5, 87.9 (C-1, C-4, 51.3 (C-2, HRMS (CI, m/z calcd for C 23H31NO13Na [M, Na, 552.1693; found: 552.1689. Selected Data for Compound 7d Pale yellow oil; 60% yield; [α]D20 +29.4 (c 0.54, CHCl 3, 1H NMR (400 MHz, CDCl3, δ, 5.57 (dd, 1 H, J1′,2′, 2.4 Hz, H-1′, 5.37 (ddd, 1 H, H-2′, 5.11 dd, 1
    • +: 488.1768; found: 488.1754.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.