Synthesis of novel 5-O-(6′-O-modified)-desosamine 14-membered ketolides

详细信息    查看全文 | 推荐本文 |

英文篇名：Synthesis of novel 5-O-(6′-O-modified)-desosamine 14-membered ketolides 作者：Zhehui ; Zhao ; Apeng ; Wang ; Xiaoxi ; Zhang ; Shuang ; Yang ; Zhigang ; Luo ; Pingsheng ; Lei 英文作者：Zhehui Zhao;Apeng Wang;Xiaoxi Zhang;Shuang Yang;Zhigang Luo;Pingsheng Lei;State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences ξ Peking Union Medical College; 英文关键词：Ketolides;;Desosamine;;Glycosyolation;;Modification 中文刊名：FXKB 英文刊名：中国化学快报(英文版) 机构：State Key Laboratory of Bioactive Substance and Function of Natural Medicines, Beijing Key Laboratory of Active Substances Discovery and Drugability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences ξ Peking Union Medical College; 出版日期：2019-02-15 出版单位：Chinese Chemical Letters 年：2019 期：v.30 基金：supported by the CAMS Innovation Fund for Medical Sciences(Nos.2017-I2M-3-011 and 2017-I2M-1-012) 语种：英文; 页：FXKB201902035 页数：3 CN：02 ISSN：11-2710/O6 分类号：175-177

摘要

A new and facile procedure was developed to synthesize novel 5-0- (6′-O-modified)-desosamine 14-membered ketolides by adopting different protective strategies and comparing various glycosylation conditions. Two trichloroacetimidate donors, with Lev or Ac substituent groups at the C-6 position, were synthesized to couple with the erythronolide. Several novel 5-0- (6′-O-modified)-desosamine 14-membered ketolides were obtained to verify the utility of the method.
        A new and facile procedure was developed to synthesize novel 5-0- (6′-O-modified)-desosamine 14-membered ketolides by adopting different protective strategies and comparing various glycosylation conditions. Two trichloroacetimidate donors, with Lev or Ac substituent groups at the C-6 position, were synthesized to couple with the erythronolide. Several novel 5-0- (6′-O-modified)-desosamine 14-membered ketolides were obtained to verify the utility of the method.

引文

[1](a)H. Takashima, Curr. Top. Med. Chem. 3(2003)991-999.
    [2](a)N. LeTourneau, P. Vimal, D. Klepacki, A. Mankin, A. Melman, Bioorg. Med.Chem. Lett. 22(2012)4575-4578.
    [3] L.T. Phan, T. Jian, Z. Chen, et al., J. Med. Chem. 47(2004)2965-2968.
    [4] A. Romero, C.H. Liang, Y.H. Chiu, et al., Tetrahedron Lett. 46(2005)1483-1487.
    [5] C.H. Liang, S. Yao, Y.H. Chiu, et al., Bioorg. Med. Chem. Lett. 15(2005)1307-1310.
    [6](a)X.Z. Chen, P. Xu, Y.P. Xu, et al., Bioorg. Med. Chem. Lett. 22(2012)7402-7405.
    [7] A.P. Wang, C. Liu, S. Yang, Z.H. Zhao, P.S. Lei, Tetrahedron 72(2016)285-297.
    [8] H. Arita, N. Ueda, Y. Matsushima, B Chem. Soc. JPN. 45(1972)567-569.
    [9] T. Yoshisuke, N. Tomoko, K. Fumiyuki, K. Yukihiko, Heterocycle 44(1997)427-433.
    [10] W.L. Chen, C.F. Xia, J.H. Wang, et al., J. Org. Chem. 72(2007)9914-9923.
    [11] P.D. Alexander, N.B. Charles, A.J.F. Michael, S.B. John, Tetrahedron Lett. 42(2001)117-119.
    [12] J. Xue, J. Wang, Z. Guo, Org. Lett. 6(2004)1365-1368.
    [13] P.B. Alper, S.C. Hung, C.H. Wong, Tetrahedron Lett. 37(1996)6029-6032.
    [14] K. Rakesh, I.W. Leonard, E.K. Edward, J. Med. Chem. 36(1993)2470-2474.
    [15] B. Luisa, N. Daniele, S. Corrado, S. Piero, J. Org. Chem. 64(1996)7836-7841.
    [16] E.F.V. Scriven, K. Turnbull, Chem. Rev. 88(1988)298-360.
    [17] B. Lusia, L. Rino, M. Matteo, et al., Tetrahedron 58(2002)3485-3492.
    [18] A. Shazia, D.V. Natasha, E.R. Joseph, R.J.P. David, Tetrahedron 69(2013)816-825.
    [19] J. Zhang, Y. Sun, X. Zhang, C. Li, H. Guan, Carbohydr. Res. 381(2013)74-82.
    [20] D. Mercedes, D.M. Julio, J. Org. Chem. 64(1999)4798-4810.