메뉴 건너뛰기




Volumn 29, Issue 21, 1988, Pages 2563-2565

Syntheses of 4(R)-silyloxy-6(S)-iodomethyl-tetrahydropyran-2-one and its enantiomer, building blocks for HMG-COA reductase inhibitors

Author keywords

[No Author keywords available]

Indexed keywords

DRUG STRUCTURE; DRUG SYNTHESIS; NONHUMAN; NUCLEAR MAGNETIC RESONANCE;

EID: 0023913858     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)86112-2     Document Type: Article
Times cited : (32)

References (30)
  • 5
    • 84918484713 scopus 로고    scopus 로고
    • W. Bartmann, G. Beck, H. Jendralla, B.v. Kerekjarto German Patent Application P 3632893.6 (1986).
  • 6
    • 84918484712 scopus 로고    scopus 로고
    • C.E. Redemann, C. Niemann, Org. Synth. Coll. Vol. III, 11.
  • 10
    • 84918484711 scopus 로고    scopus 로고
    • 1H-nmr and ms spectra.
  • 11
    • 84918484710 scopus 로고    scopus 로고
    • +, 0.5%), 437 (M-tert.-Bu), 395, 269, 225 (100%), 199, 183.
  • 14
    • 84918484709 scopus 로고    scopus 로고
    • 13 were required.
  • 15
    • 85058980593 scopus 로고    scopus 로고
    • D = + 2.15° (c= 1.0, acetone).
  • 16
    • 84981882032 scopus 로고
    • Isocyanate als universelle Reagentien bei der Derivatbildung für die gaschromatographische Enantiomerentrennung
    • ee's determined according to
    • (1982) Angewandte Chemie , vol.94 , pp. 709
    • Benecke1    König2
  • 18
    • 84918484707 scopus 로고    scopus 로고
    • 2O (3x100ml) and EtOAc (3x100ml). These extracts were dried, filtered, evaporated in vacuo to give 7.4 g 8, colorless oil.
  • 19
    • 84918484706 scopus 로고    scopus 로고
    • 2, dry acetone, 10% Pd/C, 1 atm H2, 25°C, 25 min.
  • 20
    • 84918484705 scopus 로고    scopus 로고
    • 16.
  • 21
    • 85058980457 scopus 로고    scopus 로고
    • 11.
  • 22
    • 84918484703 scopus 로고    scopus 로고
    • 2O/ n-hexane, ≤20°C.
  • 23
    • 84918484702 scopus 로고    scopus 로고
    • 2O 1:1. Rf 1′ = 1: 0.25, 13:0.19.
  • 24
    • 84918484701 scopus 로고    scopus 로고
    • 3): δ = 1.82 (m, 1H), 1.90 (d, 1H) 2.17 (dm, 1H), 2.68 (AB of ABX, 2H), 3.10 (dd, 1H), 3.30 (dd, 1H), 4.42 (qui, 1H), 4.86 (m, 1H), 7.30 (AA′BB′, 4H).
  • 25
    • 84918484700 scopus 로고    scopus 로고
    • 3 shifts the dm of one of the methylene protons at C-5 from 2.17 to 6.73 (major) and 6.62 (minor). Traces of the enantiomer of 14 are best detected at the low field part (pseudo-doublet, δ = 7.32 ppm) of the aromatic AA′BB′ system, which under these conditions shifts to 8.8 ppm. The enantiomer is seen as a shoulder at the low field end of the shifted signal.
  • 26
    • 85058980885 scopus 로고    scopus 로고
    • D = −0.27° (c= 1, acetone).
  • 27
    • 85058981069 scopus 로고    scopus 로고
    • D=+ 0.28° (c= 1, acetone).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.