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Volumn 50, Issue 30, 2009, Pages 4384-4388

First chemoenzymatic synthesis of immunomodulating macrolactam pimecrolimus

Author keywords

Ascomycin; Immunomodulator; Lipase; Macrolactam; Regioselectivity

Indexed keywords

HYDROXYL GROUP; PIMECROLIMUS; TRIACYLGLYCEROL LIPASE;

EID: 66749138208     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.05.066     Document Type: Article
Times cited : (10)

References (32)
  • 8
    • 66749152970 scopus 로고    scopus 로고
    • Baumann, K.; Emmer, G. E.P. 0, 427, 680, A1, 1991.
    • Baumann, K.; Emmer, G. E.P. 0, 427, 680, A1, 1991.
  • 12
    • 66749129424 scopus 로고    scopus 로고
    • note
    • +.
  • 13
    • 66749104911 scopus 로고    scopus 로고
    • Patent 0, 464, 895, A2, 1992. The 32-acetylation was performed with acetic anhydride in benzene and the yields were in the range of 20-30
    • Petuch, B. R.; Chen, S.-S. T.; Arison, B. H. E.P. Patent 0, 464, 895, A2, 1992. The 32-acetylation was performed with acetic anhydride in benzene and the yields were in the range of 20-30%.
    • Petuch, B.R.1    Chen, S.-S.T.2    Arison, B.H.E.P.3
  • 14
    • 66749094519 scopus 로고    scopus 로고
    • note
    • Tacrolimus is the 21-allyl analogue of ascomycin.
  • 15
    • 66749112699 scopus 로고    scopus 로고
    • note
    • +.
  • 16
    • 66749175552 scopus 로고    scopus 로고
    • note
    • +.
  • 19
    • 66749151151 scopus 로고    scopus 로고
    • note
    • +.
  • 23
    • 66749169666 scopus 로고    scopus 로고
    • note
    • +.
  • 24
    • 66749099293 scopus 로고    scopus 로고
    • note
    • 24-O-tert-Butyldimethylsilyl-ascomycin 4. Removal of 32-acetate was realized in the same conditions utilized for preparation of 24-O-acetyl-ascomycin 7 from corresponding 24,32-diacetate 6. Chemical-physical data of 4 are in agreement with those reported in literature (Ref. 5).
  • 25
    • 66749142150 scopus 로고    scopus 로고
    • note
    • The same transformation was successfully (73%) realized also with dichlorotriphenylphosphorane (Grassberger, M.; Horvath, A. WO 040111 A2, 2006) not applicable, on the contrary, in the case of 24-monoacetate 7 for the formation of a complex mixture.
  • 26
    • 0030931957 scopus 로고    scopus 로고
    • note
    • PTSA is reported (Ok, H. O.; Szumiloski, J. L., Beattie, T. R.; Goulet, M. T. Bioorg. Med. Chem. Lett. 1997, 7, 2199-2204) to selectively remove the 32-silyl group from 24,32-disilyl derivative. In this case, we observed that lower temperatures (10-15 °C instead of 25-30 °C) and shorter times (20 h instead of 72 h) were required.
  • 27
    • 66749167426 scopus 로고    scopus 로고
    • note
    • 13C NMR data were in agreement with the reported ones (Dosenbach, C.; Grassberger, M.; Hartmann, O.; Horvath, A,; Mutz, J.-P.; Penn, G.; Pfeffer, S.; Wieckhusen, D. WO 01458, 1999).
  • 29
    • 66749111026 scopus 로고    scopus 로고
    • note
    • +; pimecrolimus (exact mass 809.4) spectrum shows the main peak at 832.4 m/z.
  • 30
    • 66749127064 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra.
  • 31
    • 66749173275 scopus 로고    scopus 로고
    • note
    • 3 singlet (3.46 and 3.44), H-32 (3.68, major and minor rotamers).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.