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Volumn 72, Issue 11, 2007, Pages 4055-4066

Investigation of the regioselectivity for the Staudinger reaction and its application for the synthesis of aminoglycosides with N-1 modification

Author keywords

[No Author keywords available]

Indexed keywords

PERAZIDONEAMINE; PERAZIDORIBOSTAMYCIN; STAUDINGER REDUCTION;

EID: 34249778990     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo062588j     Document Type: Article
Times cited : (28)

References (30)
  • 1
    • 0004121735 scopus 로고
    • Umezawa, H, Hooper, I. R, Ed, Springer-Verlag: New York
    • Umezawa, S.; Tsuchiya, T. In Aminoglycoside Antibiotics; Umezawa, H., Hooper, I. R., Ed.; Springer-Verlag: New York, 1982; pp 37-110.
    • (1982) Aminoglycoside Antibiotics , pp. 37-110
    • Umezawa, S.1    Tsuchiya, T.2
  • 2
    • 0009148056 scopus 로고
    • Pigmann, H, Horton, D, Eds, Academic Press: New York/London
    • Hanessian, S.; Haskell, T. H. In Antibiotics Containing Sugars; Pigmann, H., Horton, D., Eds.; Academic Press: New York/London, 1970; pp 139-211.
    • (1970) Antibiotics Containing Sugars , pp. 139-211
    • Hanessian, S.1    Haskell, T.H.2
  • 24
    • 0033583014 scopus 로고    scopus 로고
    • The axial substituent is typically more shielded as compared to the equatorial one as indicated by the chemical shifts of H-2ax and H-2eq in this report. Similar results regarding the chemical shifts of methyl group on methylcyclohexane can be found in the literature as well Wiberg, K. B, Hammer, J. D, Castejon, H, Bailey, W. F, DeLeon, E. L, Jarret, R. M. J. Org. Chem. 1999, 64, 2085-2095, However, computational analysis of the electron density and electrostatic potential for the axial and equatorial azido groups on cyclohexane reveals only slight difference favoring equatorial azido group toward nucleophilic agent. Thus, we reason that a combination of stereoelectronic effect and steric hindrance should contribute to the lower reactivity of the N-2‴ azido group
    • eq in this report. Similar results regarding the chemical shifts of methyl group on methylcyclohexane can be found in the literature as well (Wiberg, K. B.; Hammer, J. D.; Castejon, H.; Bailey, W. F.; DeLeon, E. L.; Jarret, R. M. J. Org. Chem. 1999, 64, 2085-2095). However, computational analysis of the electron density and electrostatic potential for the axial and equatorial azido groups on cyclohexane reveals only slight difference favoring equatorial azido group toward nucleophilic agent. Thus, we reason that a combination of stereoelectronic effect and steric hindrance should contribute to the lower reactivity of the N-2‴ azido group.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.