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Volumn , Issue 1, 2008, Pages 150-155

A straightforward protocol for the solution-phase parallel synthesis of ceramide analogues

Author keywords

Amino alcohols; Ceramide analogues; Combinatorial chemistry; Scavengers; Supported reagents

Indexed keywords


EID: 38049086665     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200700814     Document Type: Article
Times cited : (6)

References (17)
  • 12
    • 38049057639 scopus 로고    scopus 로고
    • 1H NMR spectroscopy and were consistently pure enough for the next step.
    • 1H NMR spectroscopy and were consistently pure enough for the next step.
  • 14
    • 38049025572 scopus 로고    scopus 로고
    • When required, traces of unreacted starting amine were removed with the acidic resin Amberlyte IR120 hydrogen form (Aldrich, ref 216534) as follows: A solution of the corresponding ceramide analogue in MeOH (2.0 mL) was treated with Amberlyte IR120 (100 mg, equivalent to 0.4 mmol based on resin loading) and stirred overnight at room temperature. The resin was filtered out, and the solution was evaporated to dryness to afford the required ceramide analogues.
    • When required, traces of unreacted starting amine were removed with the acidic resin Amberlyte IR120 hydrogen form (Aldrich, ref 216534) as follows: A solution of the corresponding ceramide analogue in MeOH (2.0 mL) was treated with Amberlyte IR120 (100 mg, equivalent to 0.4 mmol based on resin loading) and stirred overnight at room temperature. The resin was filtered out, and the solution was evaporated to dryness to afford the required ceramide analogues.
  • 15
    • 0346363142 scopus 로고    scopus 로고
    • Formation of 7 can be interpreted as a result of an intramolecular displacement of the tert-butoxide group by a transient alkoxide. This process seems sensitive to the electronic effects of the aromatic ring, as the reaction from ρ-chloro-3-methylphenol led to an approximately 1:1 mixture of the intermediate oxazolidinone and the corresponding ceramide analogue. For a related example of this intramolecular cyclization, see: G. Triola, G. Fabrias, J. Casas, A. Llebaria, J. Org. Chem. 2003, 68, 9924-9932.
    • Formation of 7 can be interpreted as a result of an intramolecular displacement of the tert-butoxide group by a transient alkoxide. This process seems sensitive to the electronic effects of the aromatic ring, as the reaction from ρ-chloro-3-methylphenol led to an approximately 1:1 mixture of the intermediate oxazolidinone and the corresponding ceramide analogue. For a related example of this intramolecular cyclization, see: G. Triola, G. Fabrias, J. Casas, A. Llebaria, J. Org. Chem. 2003, 68, 9924-9932.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.