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Volumn 12, Issue 9, 2010, Pages 2076-2079

(2-Nitrophenyl)acetyl: A new, selectively removable hydroxyl protecting group

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EID: 77951862701     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100562f     Document Type: Article
Times cited : (27)

References (49)
  • 2
    • 0003405157 scopus 로고
    • Georg Thieme Verlag: Stuttgart and New York
    • Kocienski, P. J. Protecting Groups; Georg Thieme Verlag: Stuttgart and New York, 1994.
    • (1994) Protecting Groups
    • Kocienski, P.J.1
  • 27
    • 0003134789 scopus 로고
    • Some of the previously reported protecting groups having a nitro auxiliary function, involve the 4-methyl-4-nitropentanoyl group for hydroxyl and amine protection, see
    • Some of the previously reported protecting groups having a nitro auxiliary function, involve the 4-methyl-4-nitropentanoyl group for hydroxyl and amine protection, see: Ho, T.-L. Synth. Commun. 1980, 10, 469-472
    • (1980) Synth. Commun. , vol.10 , pp. 469-472
    • Ho, T.-L.1
  • 28
    • 0037189162 scopus 로고    scopus 로고
    • the 2,2-dimethyl-2-(o -nitrophenyl)acetyl group for amine protection, see
    • the 2,2-dimethyl-2-(o -nitrophenyl)acetyl group for amine protection, see: Jiang, Y. Y.; Zhao, J.; Hu, L. Q. Tetrahedron Lett. 2002, 43, 4589-4592
    • (2002) Tetrahedron Lett. , vol.43 , pp. 4589-4592
    • Jiang, Y.Y.1    Zhao, J.2    Hu, L.Q.3
  • 29
    • 0001365316 scopus 로고
    • the 3-(4- tert -butyl-2,6-dinitrophenyl)-2,2-dimethylpropionyl group for amine protection, see
    • the 3-(4- tert -butyl-2,6-dinitrophenyl)-2,2-dimethylpropionyl group for amine protection, see: Johnson, F.; Habus, I.; Gentles, R. G.; Shibutani, S.; Lee, H. C.; Iden, C. R.; Rieger, R. J. Am. Chem. Soc. 1992, 114, 4923-4924
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 4923-4924
    • Johnson, F.1    Habus, I.2    Gentles, R.G.3    Shibutani, S.4    Lee, H.C.5    Iden, C.R.6    Rieger, R.7
  • 30
    • 77951777452 scopus 로고    scopus 로고
    • For the use of related groups in prodrug activation by bioreduction, see
    • For the use of related groups in prodrug activation by bioreduction, see
  • 35
    • 77951817938 scopus 로고    scopus 로고
    • For reaction kinetics data and mechanistic details on the cyclization of (2-nitrophenyl)acetates and propionates, see
    • For reaction kinetics data and mechanistic details on the cyclization of (2-nitrophenyl)acetates and propionates, see
  • 43
    • 77951819066 scopus 로고    scopus 로고
    • For examples of the above transformations in the presence of the NPAc group see the Supporting Information
    • For examples of the above transformations in the presence of the NPAc group see the Supporting Information.
  • 44
    • 77951854766 scopus 로고    scopus 로고
    • Note
    • 4Cl. We assume that a Zn complex of (2-aminophenyl)acetic acid is formed. For ready formation of Zn complexes of amino acids, see
  • 46
    • 77951845055 scopus 로고    scopus 로고
    • Isolated acyl groups at O-2 of hexopyranosides are known to be relatively resistant to Zemplén deacylation. See
    • Isolated acyl groups at O-2 of hexopyranosides are known to be relatively resistant to Zemplén deacylation. See


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