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Volumn , Issue 10, 2007, Pages 1659-1668

Synthesis and conformational analysis of constrained β-turn mimetics incorporating a bicyclic turn inducer by use of the petasis three-component reaction on solid phase

Author keywords

Amino acids; Peptidomimetics; Scaffold; Solid phase synthesis

Indexed keywords


EID: 34250638277     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600650     Document Type: Article
Times cited : (13)

References (54)
  • 45
    • 34250635903 scopus 로고    scopus 로고
    • Early cleavage after treatment of the resin-bound active ester group with amine was checked by analysis of filtrate, resulting in complete stability of the resin-bound compound to this reaction step. It was supposed that the resistance of resin-bound product to early cleavage by amine treatment was mainly due to the amount of amine used in the two steps, as in the amidation reaction only 5 equiv. were used, whereas in the cleavage the amount of amine was raised to 110 equiv
    • Early cleavage after treatment of the resin-bound active ester group with amine was checked by analysis of filtrate, resulting in complete stability of the resin-bound compound to this reaction step. It was supposed that the resistance of resin-bound product to early cleavage by amine treatment was mainly due to the amount of amine used in the two steps, as in the amidation reaction only 5 equiv. were used, whereas in the cleavage the amount of amine was raised to 110 equiv.
  • 48
    • 34250686205 scopus 로고    scopus 로고
    • Diastereoselectivity was determined immediately after the Petasis reaction by treatment of the resulting COOH group with TMS/diazomethane in CH2Cl2/MeOH as solvent system for 2 h, followed by cleavage from the resin. The resulting de value of 87% was consistent with a lack of epimerization during the COOH activation with DIC/HOBt
    • 2/MeOH as solvent system for 2 h, followed by cleavage from the resin. The resulting de value of 87% was consistent with a lack of epimerization during the COOH activation with DIC/HOBt.
  • 49
    • 34250679759 scopus 로고    scopus 로고
    • The conformational analysis on major diastereomers of 2 and 4 were performed on enriched mixtures of such compounds.
    • The conformational analysis on major diastereomers of 2 and 4 were performed on enriched mixtures of such compounds.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.