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Volumn 3, Issue 1, 2001, Pages 117-124

Polytetrahydrofuran cross-linked polystyrene resins for solid-phase organic synthesis

Author keywords

[No Author keywords available]

Indexed keywords

CROSS LINKING REAGENT; FURAN DERIVATIVE; POLYSTYRENE DERIVATIVE;

EID: 0035228613     PISSN: 15204766     EISSN: None     Source Type: Journal    
DOI: 10.1021/cc000083f     Document Type: Article
Times cited : (83)

References (90)
  • 31
    • 0032469083 scopus 로고    scopus 로고
    • Lebl, M. Biopolymers 1998, 47, 397-404.
    • (1998) Biopolymers , vol.47 , pp. 397-404
    • Lebl, M.1
  • 50
    • 0039302819 scopus 로고    scopus 로고
    • Resins containing 2 mol % cross-linking by 3a and functionalized with chloromethyl, hydroxymethyl, aminomethyl, and Wang linker groups are commercially available from the Aldrich Chemical Co. under the JandaJel name.
    • Resins containing 2 mol % cross-linking by 3a and functionalized with chloromethyl, hydroxymethyl, aminomethyl, and Wang linker groups are commercially available from the Aldrich Chemical Co. under the JandaJel name.
  • 52
    • 0031885783 scopus 로고    scopus 로고
    • At the time of the initiation of this project no reports using PTHF based cross-linking agents had appeared. Pillai has subsequently reported the use of THF-acrylate cross-linkers for solid-phase peptide resins. These cross-linkers were designed to impart added polarity and therefore presumably make the resins prepared from them more suitable for the solid-phase synthesis of nonpolar peptide sequences. In fact, their hypothesis was validated in that their resins afforded improved product yields and purities. Since these cross-linkers contain ester linkages, they would be incompatible in SPOS when highly basic conditions are required. (a) Varkey, J. T.; Pillai, V. N. R. J. Pept. Res. 1998, 51, 49-54.
    • (1998) J. Pept. Res. , vol.51 , pp. 49-54
    • Varkey, J.T.1    Pillai, V.N.R.2
  • 56
  • 58
    • 0026189348 scopus 로고
    • The synthesis of 2c is reported by Robin et al., but attempts to repeat this procedure failed to afford the desired product in high yield or in a pure state. Bougherara, C.; Boutevin, B.; Robin, J.-J. Polym. Bull. (Berlin) 1991, 26, 181-185.
    • (1991) Polym. Bull. (Berlin) , vol.26 , pp. 181-185
    • Bougherara, C.1    Boutevin, B.2    Robin, J.-J.3
  • 67
    • 0039895020 scopus 로고    scopus 로고
    • Complete swelling data for 1, 2, 5, and 10% cross-linked resins 5a-c has previously been reported (ref 23) and for convenience is reproduced in the Supporting Information of this manuscript (Table S1).
    • Complete swelling data for 1, 2, 5, and 10% cross-linked resins 5a-c has previously been reported (ref 23) and for convenience is reproduced in the Supporting Information of this manuscript (Table S1).
  • 78
    • 0001295966 scopus 로고
    • Traditionally, hydroxymethyl resins for SPOS have been prepared from chloromethyl resin by a two-step procedure of esterification and hydrolysis [(a) Martin, G. E.; Shambhu, M. B.; Shakhshir, S. R.; Digenis, G. A. J. Org. Chem. 1978, 43, 4571-4574.
    • (1978) J. Org. Chem. , vol.43 , pp. 4571-4574
    • Martin, G.E.1    Shambhu, M.B.2    Shakhshir, S.R.3    Digenis, G.A.4
  • 81
    • 0031245911 scopus 로고    scopus 로고
    • (d) Sheng, Q.; Stover, H. D. H. Macromolecules 1997, 30, 6451-6457)], or polymerization of a 4-vinylbenzyl ester monomer [
    • (1997) Macromolecules , vol.30 , pp. 6451-6457
    • Sheng, Q.1    Stover, H.D.H.2
  • 83
    • 0023961207 scopus 로고
    • (f) Beinhoffer, T. W.; Glass, J. E. J. Polym. Sci. Part A, Polym. Chem. 1988, 26, 343-353)]. In keeping with our strategy to directly prepare functionalized resins by incorporating functionalized monomers in the polymerization reactions, we found that 4-vinylbenzyl alcohol was suitable for introducing the hydroxymethyl functionality and that protection of the alcohol monomer was unnecessary.
    • (1988) J. Polym. Sci. Part A, Polym. Chem. , vol.26 , pp. 343-353
    • Beinhoffer, T.W.1    Glass, J.E.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.