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Volumn 16, Issue 9, 1997, Pages 1393-1406

Synthesis of 1-O-(methylthio)thiocarbonyl sugar derivatives bearing acyl protective groups using phase transfer catalysis methods

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EID: 0031323963     PISSN: 07328303     EISSN: None     Source Type: Journal    
DOI: 10.1080/07328309708005757     Document Type: Article
Times cited : (1)

References (41)
  • 18
    • 0017818691 scopus 로고
    • A few aminoglycoside antibiotics containing benzoyl protective groups are known to be O-(methylthio)thiocarbonylated under basic condition in low yields: for example see T. Hayashi, T. Iwaoka, N. Takeda and E. Ohki, Chem. Pharm. Bull., 26, 1786 (1978).
    • (1978) Chem. Pharm. Bull. , vol.26 , pp. 1786
    • Hayashi, T.1    Iwaoka, T.2    Takeda, N.3    Ohki, E.4
  • 25
    • 1842273840 scopus 로고    scopus 로고
    • Some examples used for sugar derivatives : J. P. Ferris, S. Singh and T. A. Newton, J. Org. Chem., 44, 173 (1979); D. Dess, H. P. Kleine, D. V. Weinberg, R. J. Kaufman and R. S. Sidhu, Synthesis, 883 (1981); D. Loganathan, A. J. Amonkar and G. K. Trivedi, Ind. J. Chem., 22B, 400 (1983).
    • (1979) J. Org. Chem. , vol.44 , pp. 173
    • Ferris, J.P.1    Singh, S.2    Newton, T.A.3
  • 26
    • 1842273840 scopus 로고    scopus 로고
    • Some examples used for sugar derivatives : J. P. Ferris, S. Singh and T. A. Newton, J. Org. Chem., 44, 173 (1979); D. Dess, H. P. Kleine, D. V. Weinberg, R. J. Kaufman and R. S. Sidhu, Synthesis, 883 (1981); D. Loganathan, A. J. Amonkar and G. K. Trivedi, Ind. J. Chem., 22B, 400 (1983).
    • Synthesis , vol.883 , pp. 1981
    • Dess, D.1    Kleine, H.P.2    Weinberg, D.V.3    Kaufman, R.J.4    Sidhu, R.S.5
  • 27
    • 1842273840 scopus 로고    scopus 로고
    • Some examples used for sugar derivatives : J. P. Ferris, S. Singh and T. A. Newton, J. Org. Chem., 44, 173 (1979); D. Dess, H. P. Kleine, D. V. Weinberg, R. J. Kaufman and R. S. Sidhu, Synthesis, 883 (1981); D. Loganathan, A. J. Amonkar and G. K. Trivedi, Ind. J. Chem., 22B, 400 (1983).
    • (1983) Ind. J. Chem. , vol.22 B , pp. 400
    • Loganathan, D.1    Amonkar, A.J.2    Trivedi, G.K.3
  • 28
    • 0001165001 scopus 로고    scopus 로고
    • Solid - liquid two phase methods are known to be milder than liquid - liquid two phase methods: for examples see M. Fedorynski, K. Wojciechowski, Z. Matacz and M. Makosza, J. Org. Chem., 43, 4682 (1978); V. G. Purohit and R. Subramanian, Chem. Ind., 731 (1978); G. V. Kryshtal, V. V. Kulganek, V. F. Kucherov and L. A. Yanovskaya, Synthesis, 107 (1979).
    • (1978) J. Org. Chem. , vol.43 , pp. 4682
    • Fedorynski, M.1    Wojciechowski, K.2    Matacz, Z.3    Makosza, M.4
  • 29
    • 0001165001 scopus 로고    scopus 로고
    • Solid - liquid two phase methods are known to be milder than liquid - liquid two phase methods: for examples see M. Fedorynski, K. Wojciechowski, Z. Matacz and M. Makosza, J. Org. Chem., 43, 4682 (1978); V. G. Purohit and R. Subramanian, Chem. Ind., 731 (1978); G. V. Kryshtal, V. V. Kulganek, V. F. Kucherov and L. A. Yanovskaya, Synthesis, 107 (1979).
    • (1978) Chem. Ind. , pp. 731
    • Purohit, V.G.1    Subramanian, R.2
  • 30
    • 0001165001 scopus 로고    scopus 로고
    • Solid - liquid two phase methods are known to be milder than liquid - liquid two phase methods: for examples see M. Fedorynski, K. Wojciechowski, Z. Matacz and M. Makosza, J. Org. Chem., 43, 4682 (1978); V. G. Purohit and R. Subramanian, Chem. Ind., 731 (1978); G. V. Kryshtal, V. V. Kulganek, V. F. Kucherov and L. A. Yanovskaya, Synthesis, 107 (1979).
    • Synthesis , vol.107 , pp. 1979
    • Kryshtal, G.V.1    Kulganek, V.V.2    Kucherov, V.F.3    Yanovskaya, L.A.4
  • 32
    • 3142605395 scopus 로고    scopus 로고
    • note
    • 36 (dropwise addition of benzoyl chloride to a dichloromethane solution of the latter compound in the presence of pyridine): syrup, 60 % yield, α/β = 1 : 3.
  • 33
    • 3142573210 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum.
  • 34
    • 3142599291 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum and thin-layer chromatogram of the mixture indicated the presence only of 2α and 2β.
  • 36
    • 3142530970 scopus 로고    scopus 로고
    • note
    • Commercially available material (Aldrich Chemical Company, Inc.).
  • 38
    • 0002748511 scopus 로고
    • A. Marra and P. Sinaÿ, Carbohydr. Res., 187, 35 (1989); T. Ercégovic and G. Magnusson, J. Org. Chem., 60, 3378 (1995).
    • (1989) Carbohydr. Res. , vol.187 , pp. 35
    • Marra, A.1    Sinaÿ, P.2
  • 40
    • 3142637195 scopus 로고    scopus 로고
    • note
    • Recent reinvestigation on the anomeric configuration of the compound 4α using a 270MHz-NMR apparatus revealed that 4α has the a configuration. The corresponding compound 4β in the reference 23 should be read as compound 4α.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.