메뉴 건너뛰기




Volumn 19, Issue 24, 2008, Pages 2907-2912

Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. III: synthesis of enantiopure methyl (1S,2S,3R,4S,5R)-2-amino-3,4,5-trihydroxycyclopentanecarboxylate

Author keywords

[No Author keywords available]

Indexed keywords

2 OXABICYCLO[2.2.1]HEPTANE; CARBOXYLIC ACID DERIVATIVE; CYCLOPENTYLAMINE; FURAN DERIVATIVE; HEPTANE DERIVATIVE; METHYL 2 AMINO 3,4,5 TRIHYDROXYCYCLOPENTANECARBOXYLATE; NITROHEXOFURANOSE; PENTYLAMINE; SUGAR; UNCLASSIFIED DRUG;

EID: 59349089385     PISSN: 09574166     EISSN: 1362511X     Source Type: Journal    
DOI: 10.1016/j.tetasy.2008.12.017     Document Type: Article
Times cited : (11)

References (28)
  • 2
    • 33746329886 scopus 로고    scopus 로고
    • For reviews, see:
    • For reviews, see:. Jarosz S. Chim. Oggi 24 (2006) 58-61
    • (2006) Chim. Oggi , vol.24 , pp. 58-61
    • Jarosz, S.1
  • 6
    • 0001222924 scopus 로고
    • Knapp S. Chem. Rev. 95 (1995) 1859-1876
    • (1995) Chem. Rev. , vol.95 , pp. 1859-1876
    • Knapp, S.1
  • 17
    • 0043268074 scopus 로고    scopus 로고
    • For the first total synthesis of polyhydroxylated cyclopentane β-amino acids, see:
    • For the first total synthesis of polyhydroxylated cyclopentane β-amino acids, see:. Soengas R.G., Estevez J.C., and Estevez R.J. Org. Lett. 5 (2003) 1423-1425
    • (2003) Org. Lett. , vol.5 , pp. 1423-1425
    • Soengas, R.G.1    Estevez, J.C.2    Estevez, R.J.3
  • 20
    • 59349090675 scopus 로고    scopus 로고
    • note
    • Crystallographic data for the structure of compound 12b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-205610. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
  • 21
    • 59349100954 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of the epimeric mixture 12a + 12b displayed two singlets at 3.41 ppm and 3.49, both due to the anomeric OMe substituents, respectively. A ratio 1.1:1.0 for both anomers was deduced from these signals.
  • 22
    • 59349113261 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum of the mixture 13+14 includes two signals at 4.70 ppm and at 4.85 ppm, corresponding to the H-3 protons of anomers 13. The signal displayed at 9.45 ppm was attributed to the aldehyde proton of compound 14.
  • 26
    • 59349094583 scopus 로고    scopus 로고
    • note
    • InsightII, and Discover are trademarks of Accelrys Corp., 2002, San Diego, CA 92121, 2002.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.