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Volumn 74, Issue 16, 2009, Pages 6350-6353

Diastereoselective synthesis of γ-amino-δ-hydroxy-α, α-difluorophosphonates: A vehicle for structureactivity relationship studies on SMA-7, a potent sphingomyelinase inhibitor

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ALCOHOLS; CHEMICAL EQUATIONS; DIASTEREOSELECTIVE SYNTHESIS; PHOSPHONATES; POTENT INHIBITOR; SPHINGOMYELINASE; STRUCTURE ACTIVITY RELATIONSHIPS;

EID: 70349125444     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9008782     Document Type: Article
Times cited : (14)

References (33)
  • 13
    • 33644904578 scopus 로고    scopus 로고
    • Katsumura and co-workers independently reported that the DFMP analogue of sphingomyelin inhibits SMase competitively, see
    • Katsumura and co-workers independently reported that the DFMP analogue of sphingomyelin inhibits SMase competitively, see: Hakogi, T.; Yamamoto, T.; Fujii, S.; Ikeda, K.; Katsumura, S. Tetrahedron Lett. 2006, 47, 2627.
    • (2006) Tetrahedron Lett. , vol.47 , pp. 2627
    • Hakogi, T.1    Yamamoto, T.2    Fujii, S.3    Ikeda, K.4    Katsumura, S.5
  • 26
    • 70349131018 scopus 로고    scopus 로고
    • note
    • Yields refers to those from crude aldehyde 2 and not optimized.
  • 27
    • 70349083186 scopus 로고    scopus 로고
    • note
    • An accurate yield was not caluculated because of some inseparable impurities included.
  • 28
    • 70349121152 scopus 로고    scopus 로고
    • note
    • For the preparation of amino ketones 5, we have synthesized the Weinreb amide derived from alcohol 11 and examined the reaction with a large excess of vinyl magnesium bromide (THF/0 °C to rt). However, the Weinreb amide was found to be inert to the Grignad reagent under our experimental conditions. In a series of the phosphonothiate analogues, we failed to prepare the correponding carboxylate due to significant decomposition of 12 during oxidation. Therefore, we could not examine the reactivity of the Weinreb amide, derived from alcohol 12, to the Grignard reagent.
  • 29
    • 0026730481 scopus 로고
    • To obtain the required amino alcohol derivertives in a stereoselective manner, an alternative method may be available on the basis of sequential DIBAL-mediated reduction and alkylation with a Grignard reaction toward amino esters in one pot. (a)
    • To obtain the required amino alcohol derivertives in a stereoselective manner, an alternative method may be available on the basis of sequential DIBAL-mediated reduction and alkylation with a Grignard reaction toward amino esters in one pot. (a) Polt, R.; Peterson, M. A.; DeYong, L. J. Org. Chem. 1992, 57, 5469.
    • (1992) J. Org. Chem. , vol.57 , pp. 5469
    • Polt, R.1    Peterson, M.A.2    DeYong, L.3
  • 30
    • 0025003890 scopus 로고
    • However, in the present studies, we focused on the alkylation- oxidationreduction sequence starting from aldehydes 1 and 2
    • (b) Polt, R.; Peterson, M. A. Tetraherdon Lett. 1990, 31, 4985. However, in the present studies, we focused on the alkylation-oxidationreduction sequence starting from aldehydes 1 and 2.
    • (1990) Tetraherdon Lett. , vol.31 , pp. 4985
    • Polt, R.1    Peterson, M.A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.