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Volumn 9, Issue 6, 2007, Pages 1141-1144

Polymer-supported (2,6-dichloro-4-alkoxyphenyl)(2,4-dichlorophenyl) methanol: A new linker for solid-phase organic synthesis

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; AMINE; BENZHYDRYL DERIVATIVE; CARBOXYLIC ACID; CROSS LINKING REAGENT; HYDROXYTETRACHLORODIPHENYLMETHYL; PHENOL; POLYMER; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

EID: 33947583428     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070150f     Document Type: Article
Times cited : (19)

References (30)
  • 19
    • 33947610280 scopus 로고    scopus 로고
    • The MM2 calculation of 4d (R4, Me) indicated that the dihedral angle formed by two planar chloro-substituted benzenes is 76.4°. The -CO-O- linkage and the ether methine proton would preferentially be in a common plane. Thus, the chloro atoms at ortho positions of two benzenes hinder the nucleophilc attack on the carbonyl group of the esters
    • 4 = Me) indicated that the dihedral angle formed by two planar chloro-substituted benzenes is 76.4°. The -CO-O- linkage and the ether methine proton would preferentially be in a common plane. Thus, the chloro atoms at ortho positions of two benzenes hinder the nucleophilc attack on the carbonyl group of the esters.
  • 20
    • 0004138760 scopus 로고
    • For solvolytic displacement reactions with TFA, see: a
    • For solvolytic displacement reactions with TFA, see: (a) Milne, J. B. J. Chem. Non-Aqueous Solvents 1978, 5B, 1.
    • (1978) J. Chem. Non-Aqueous Solvents , vol.5 B , pp. 1
    • Milne, J.B.1
  • 22
    • 33947591428 scopus 로고    scopus 로고
    • Lantern (trademark of Mimotopes Pty, Ltd) is cylindrical in appearance and polystyrene grafted surface
    • Lantern (trademark of Mimotopes Pty, Ltd) is cylindrical in appearance and polystyrene grafted surface.
  • 23
    • 33947582971 scopus 로고    scopus 로고
    • 1H NMR analysis, using an internal standard (1-bromo-4-methoxybenzene).
    • 1H NMR analysis, using an internal standard (1-bromo-4-methoxybenzene).
  • 25
  • 26
    • 33947599867 scopus 로고    scopus 로고
    • In our hands, the synthesis of the same pentapetide with the HMBA linker employing the Fmoc-strategy afforded the desired product in ∼15
    • In our hands, the synthesis of the same pentapetide with the HMBA linker employing the Fmoc-strategy afforded the desired product in ∼15%.
  • 27
    • 33947609674 scopus 로고    scopus 로고
    • The same experiments were performed using 8b-C2 and we obtained compatible results that were observed with 8a-C2.
    • The same experiments were performed using 8b-C2 and we obtained compatible results that were observed with 8a-C2.
  • 29
    • 33947591059 scopus 로고    scopus 로고
    • The resin 8a-C2-Cl could be stored for over 20 days without decrease of the loading efficiency.
    • The resin 8a-C2-Cl could be stored for over 20 days without decrease of the loading efficiency.
  • 30
    • 33947596182 scopus 로고    scopus 로고
    • Phenolic alcohols reacted with 8a-C2-Cl-Me much faster than alkanols; greater than 90% selectivity was observed in the competition experiments with 15 and 19.
    • Phenolic alcohols reacted with 8a-C2-Cl-Me much faster than alkanols; greater than 90% selectivity was observed in the competition experiments with 15 and 19.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.