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Volumn 130, Issue 27, 2008, Pages 8769-8772

Acyl group migration and cleavage in selectively protected β-D-galactopyranosides as studied by NMR spectroscopy and kinetic calculations

Author keywords

[No Author keywords available]

Indexed keywords

ESTERIFICATION; ESTERS; NUCLEAR MAGNETIC RESONANCE; ORGANIC COMPOUNDS; SYSTEM STABILITY;

EID: 46949083185     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja801177s     Document Type: Article
Times cited : (81)

References (45)
  • 3
    • 84859253317 scopus 로고    scopus 로고
    • Bashkin, J. K. Chem. Rev. 2000, 100, 4265-4712; Ed. Special Issue.
    • (c) Bashkin, J. K. Chem. Rev. 2000, 100, 4265-4712; Ed. Special Issue.
  • 8
    • 0003405157 scopus 로고    scopus 로고
    • 3rd ed, Georg Thieme Verlag: Stuttgart, Germany
    • (d) Kocienski, P. J. Protecting Groups, 3rd ed.; Georg Thieme Verlag: Stuttgart, Germany, 2005.
    • (2005) Protecting Groups
    • Kocienski, P.J.1
  • 13
  • 16
    • 0002330018 scopus 로고    scopus 로고
    • Kurahashi, T.; Mizutani, T.; Yoshida, J.-i J. Chem. Soc., Perkin Trans. 1 1999, 465-473.
    • (e) Kurahashi, T.; Mizutani, T.; Yoshida, J.-i J. Chem. Soc., Perkin Trans. 1 1999, 465-473.
  • 32
    • 46949101879 scopus 로고    scopus 로고
    • Compounds 1-3 were prepared according to a modified literature procedure starting from D-galactose for detailed synthesis and characterization see ref 15a and Supporting Information, Peracetylation of D-galactose followed by transformation of the anomeric acetyl into benzyl ether, deacetylation, TBDPS protection of the primary hydroxyl group, introduction of the 3,4-O-acetal and ester protection of 2-OH and the subsequent silyl ether deprotection by TBAF and isopropylidene removal using Dowex H+ provided the corresponding model compounds 1-3 in approximately 40% overall yields over eight steps
    • + provided the corresponding model compounds 1-3 in approximately 40% overall yields over eight steps.
  • 39
    • 0001929604 scopus 로고    scopus 로고
    • 1H NMR spectra for all of the synthesized and purified compounds were analyzed with PERCH NMR software for complete spectral analyses, see: Laatikainen, R.; Niemitz, M.; Weber, U.; Sundelin, J.; Hassinen, T.; Vepsäläinen, J. J. Magn. Reson. Ser. A 1996, 120, 1-10. The acyl group migration was followed with Varian 500 and 600 MHz (equipped with a cold probe) Inova Spectrometers and the migration products assigned by standard 2D NMR techniques.
    • 1H NMR spectra for all of the synthesized and purified compounds were analyzed with PERCH NMR software for complete spectral analyses, see: Laatikainen, R.; Niemitz, M.; Weber, U.; Sundelin, J.; Hassinen, T.; Vepsäläinen, J. J. Magn. Reson. Ser. A 1996, 120, 1-10. The acyl group migration was followed with Varian 500 and 600 MHz (equipped with a cold probe) Inova Spectrometers and the migration products assigned by standard 2D NMR techniques.
  • 40
    • 2142715897 scopus 로고    scopus 로고
    • The model predictions were obtained by solving the differential equations for all of the components during the parameter estimation. A stiff ODE-solver was used to solve the system of ODEs, with the backward difference method implemented in the MODEST software used in the estimation of the kinetic parameters, see: Haario, H. Modest 6.0-A User's Guide; ProfMath: Helsinki, 2001. See also: Mastihubová, M.; Biely, P. Carbohydr. Res. 2004, 339, 1353-1360.
    • The model predictions were obtained by solving the differential equations for all of the components during the parameter estimation. A stiff ODE-solver was used to solve the system of ODEs, with the backward difference method implemented in the MODEST software used in the estimation of the kinetic parameters, see: Haario, H. Modest 6.0-A User's Guide; ProfMath: Helsinki, 2001. See also: Mastihubová, M.; Biely, P. Carbohydr. Res. 2004, 339, 1353-1360.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.