메뉴 건너뛰기




Volumn 46, Issue 27, 2005, Pages 4667-4670

2-Oxo-1,2-ethylenedioxy group as a linker for solution-, liquid-, and solid-phase syntheses to discover drug-like small molecules

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; ETHYLENE DERIVATIVE; FUNCTIONAL GROUP; HYDROXIDE; MACROGOL DERIVATIVE; POLYMER; RESIN;

EID: 20344397111     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.04.138     Document Type: Article
Times cited : (5)

References (26)
  • 16
    • 20344394518 scopus 로고    scopus 로고
    • note
    • MPEG-OH, HM resin, and SynPhase™ Lanterns were purchased from Aldrich Co. (catalog no. 20251-7), Advanced ChemTech, Inc. (catalog no. SA5020), and Mimotopes Pty Ltd (catalog no. SP-PS-L-HOM-015), respectively
  • 17
    • 20344402643 scopus 로고    scopus 로고
    • note
    • Polymers were recovered after the reactions by precipitation using diethyl ether for the liquid-phase synthesis, and by a simple washing in a stopcock-connected column for the solid-phase synthesis
  • 18
    • 20344388632 scopus 로고    scopus 로고
    • note
    • A stepwise reaction comprising acylation with bromoacetic acid followed by nucleophilic addition of phenol-type nucleophile is also effective. For the synthesis of 3B (MPEG) and 3C (HM resin), the loading proceeded in good yield (89%) and in poor yield (25%), respectively. The low yields are due to low reactivity of phenols toward alkyl bromide on the cross-linked polymer. Since various derivatives can be commercially available for phenol, we are now investigating high yield loading procedure via nucleophilic addition of phenol derivatives
  • 19
    • 0037427332 scopus 로고    scopus 로고
    • As can be seen in run 1, (2-naphthyloxy)acetyl group is potentially useful for an efficient protecting group of hydroxy functionality. For phenoxyacetyl group for protection of secondary alcohol, see; K. Shimada, Y. Kaburagi, and T. Fukuyama J. Am. Chem. Soc. 125 2003 4048 4049
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 4048-4049
    • Shimada, K.1    Kaburagi, Y.2    Fukuyama, T.3
  • 20
    • 20344392517 scopus 로고    scopus 로고
    • note
    • 2, the cleavage in various solvents is under investigation
  • 21
    • 20344392273 scopus 로고    scopus 로고
    • note
    • 2, allylamine, ethylenediamine, and piperidine were also effective for the cleavage
  • 26
    • 0031661388 scopus 로고    scopus 로고
    • A solution-phase Ugi-type three-component coupling reaction using perchloric acid has been reported, see; H. Bienayme, and K. Bouzid Angew. Chem., Int. Ed. 37 1998 2234 2237
    • (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2234-2237
    • Bienayme, H.1    Bouzid, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.