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Volumn 70, Issue 17, 2005, Pages 6757-6774

A stereoselective synthesis of phosphinic acid phosphapeptides corresponding to glutamyl-γ-glutamate and incorporation into potent inhibitors of folylpoly-γ-glutamyl synthetase

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; CARBOXYLIC ACIDS; CHROMATOGRAPHIC ANALYSIS; PURIFICATION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

EID: 23644459646     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0507439     Document Type: Article
Times cited : (64)

References (82)
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    • (1984) Folates and Pterins , vol.1 , pp. 135-190
    • McGuire, J.J.1    Coward, J.K.2
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    • Jackman, A. L., Ed.; Humana Press: Totowa, New Jersey
    • Jansen, G. In Antifolate Drugs in Cancer Therapy; Jackman, A. L., Ed.; Humana Press: Totowa, New Jersey, 1999; pp 293-321.
    • (1999) Antifolate Drugs in Cancer Therapy , pp. 293-321
    • Jansen, G.1
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    • 33645184089 scopus 로고    scopus 로고
    • Ph.D. Dissertation, University of Michigan, Ann Arbor, MI
    • Bartley, D. M. Ph.D. Dissertation, University of Michigan, Ann Arbor, MI, 2004.
    • (2004)
    • Bartley, D.M.1
  • 43
    • 33645175124 scopus 로고    scopus 로고
    • note
    • The checkers of the Organic Synthesis procedure also reported seeing a large amount of rearrangement but attributed it to the silica gel used during the purification; however, we observed the rearrangement products in the NMR spectra of the crude reaction mixture prior to purification.
  • 45
    • 33645174786 scopus 로고
    • 44 See Supporting Information for details.
    • (1993) Synthesis , pp. 1065
  • 46
    • 33645186988 scopus 로고    scopus 로고
    • note
    • III chemistry proved much more difficult than was anticipated. Compound 16 could easily be converted into the corresponding mesylate or tosylate in good yield by treatment with the corresponding sulfonyl chloride and pyridine. However, the triflate and iodide could be synthesized only in low yield and the resulting product decomposed at room temperature within minutes, presumable through a nonclassical carbocation intermediate. Ultimately, conditions were optimized for synthesis of the corresponding bromide (Table 2). See Supporting Information for details.
  • 53
    • 33645168644 scopus 로고    scopus 로고
    • note
    • After 18 h at room temperature only a very small amount of product (2%) was observed.
  • 60
    • 33645176814 scopus 로고    scopus 로고
    • Ph.D. Dissertation, University of Michigan, Ann Arbor, MI
    • Alexander, M. D. Ph.D. Dissertation, University of Michigan, Ann Arbor, MI, 2004.
    • (2004)
    • Alexander, M.D.1
  • 70
    • 33645181268 scopus 로고    scopus 로고
    • Mitusbishi Petrochemical Co. Ltd., Japanese Patent 59152347, 1984
    • Mitusbishi Petrochemical Co. Ltd., Japanese Patent 59152347, 1984.
  • 79
    • 33645178873 scopus 로고    scopus 로고
    • note
    • Subsequent reactions (Scheme 19) were carried out separately on compounds derived from either 64 (A series, even numbers) or 65 (B series, odd numbers).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.