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Volumn 65, Issue 10, 2000, Pages 2951-2958

Total synthesis of cyclosporin O both in solution and in the solid phase using novel thiazolium-, immonium-, and pyridinium-type coupling reagents: BEMT, BDMP, and BEP

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOSPORIN DERIVATIVE; CYCLOSPORIN O; PYRIDINIUM DERIVATIVE; REAGENT; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0342656979     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo991687c     Document Type: Article
Times cited : (45)

References (39)
  • 1
    • 84945023382 scopus 로고
    • Nomenclature and symbols of amino acids and peptides generally follow the recommendations of the IUPAC-IUB Joint Commission of Biochemical Nomenclature in: Pure Appl. Chem. 1984, 56, 595-624. The following additional abbreviations are used: Aib, α-aminoisobutyric acid; AOMP, 5-(1H-7-azabenzotriazol-1-yloxy)-3,4-dihydro-1-methyl 2H-pyrrolium hexachloroantimonate; BDMP, 5-(1H-benzotriazol-1-yloxy)-3,4-dihydro-1-methyl 2H-pyrrolium hexachloroantimonate; BEMT, 2-bromo-3-ethyl-4-methylthiazolium tetrafluoroborate; BEP, 2-bromo-1-ethyl pyridinium tetrafluoroborate; BOMI, N-(1H-benzotriazol-1-ylmethylene)-N-methylmethanaminium hexachloroantimonate N-oxide; BOP, (1H-benzotriazol-1-yloxy)tris(dimethylammo)phosphonium hexafluorophosphate; BPMP, 1-(1H-benzotriazol-1-yloxy)phenylmethylenepyrrolidinium hexachloroantimonate; BTFFH, 1,1,3,3-bis-(tetramethylene)florouronium hexafluorophosphate; CMMM, chloro(4-morphoino)methylenemorpholinium hexafluorophosphate; DIEA, N, N′-diisopropylethylamine; HAPyU, 1-(1-pyrrolidinyl-1H -1,2,3-triazolo-[4,5-b]pyridin-1-ylmethylene)pyrrolidinium hexafluorophosphate N-oxide; HBPyU, O-(1H-benzotriazol-1-yl)-N,N,N′,N′-bis(tetramethylene)-uronium hexafluorophosphate; HBTU, N-[(1H-benzotriazol-1-yl)(dimethylamino)methylene]-N-methylmethanaminium hexafluorophosphate N-oxide; HOBt, 1-hydroxybenzotriazole; MeBmt, (4R)-4-[(2′E)-butenyl]-4,N-dimethyl-L-threonine; PyBroP, bromotripyrrolidinophosphonium hexafluorophosphate.
    • (1984) Pure Appl. Chem. , vol.56 , pp. 595-624
  • 5
    • 0002339624 scopus 로고
    • White, D. J. G., Ed.; Elsevier Biomedical: Amsterdam
    • (a) Borel, J. F. In Cyclosporine A; White, D. J. G., Ed.; Elsevier Biomedical: Amsterdam, 1982; pp 5-17.
    • (1982) Cyclosporine A , pp. 5-17
    • Borel, J.F.1
  • 22
    • 0342998518 scopus 로고    scopus 로고
    • note
    • The quantity of the D-L isomer can be calculated from the four sharp signals of OMe group. The diastereoisomers: Z-L-MeVal-L-MeVal-OMe, Z-D-MeVal-L-MeVal-OMe, and Z-D,L-Me-Val-L-Me-Val-OMe were synthesized, respectively, to determine the chemical shifts and proportions of the OMe signals of the four conformers of each isomer.
  • 23
    • 0342564143 scopus 로고    scopus 로고
    • note
    • w) values were 0.045 (0.057) for 2247 reflections |I > 3.00σ(I)) and 190 variables.
  • 24
    • 0342564141 scopus 로고    scopus 로고
    • note
    • For analogous BDMP, BPMP, and AOMP of which X-ray data have not yet been obtained, the structural representations have arbitrarily been assigned as the O-substituted forms, and their nomenclature was also retained in this paper.
  • 31
    • 0343869839 scopus 로고    scopus 로고
    • Quesniaux, V. International Patent WO 86/02080, filled 9/27/85, published 4/10/86
    • Rosenthaler, J.; Wenger, R.; Ball, P. E.; Schreier, M. H.; Quesniaux, V. International Patent WO 86/02080, filled 9/27/85, published 4/10/86.
    • Rosenthaler, J.1    Wenger, R.2    Ball, P.E.3    Schreier, M.H.4
  • 32
    • 0342998512 scopus 로고    scopus 로고
    • note
    • (a) For quantitation of Fmoc-protected peptide segment on resin, UV absorbance of the fulvene-piperidine adduct at 301 nm was measured after cleavage of the Fmoc group with piperidine.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.