Synthesis of Optically Pure Macroheterocycle with Ester and Hydrazide Fragments on the Basis of l-Menthol

被引：3
|
作者：
Ishmuratov, Gumer Yu. [1 ]
Yakovleva, Marina P. [1 ]
Mingaleeva, Galina R. [1 ]
Shutova, Mariya A. [1 ]
Muslukhov, Rinat R. [1 ]
Viripaev, Evgeny M. [1 ]
Tolstikov, Alexander G. [1 ]
机构：
[1] RAS, Ufa Sci Ctr, Inst Organ Chem, Ufa 450054, Russia
来源：
MACROHETEROCYCLES | 2012年 / 5卷 / 03期
关键词：
l-Menthol; O; N-macroheterocycles; ester and hydrazide functions; synthesis;
D O I：
10.6060/mhc2012.120359y
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Based on l-menthol we have developed a synthesis method for potentially useful optically pure methyl-and isopropylbranched 21-member macrolide with hydrazide and ester fragments via sequential [2+1]-condensation of methyl-(3R, 6S)-6-hydroxy-3,7-dimethyl octanoate with glutaric acid chloranhydride and [1+1]-reaction of intermediate tetraester with hydrazine hydrate. The evidence is given for the structure of the obtained macrocycle using IR and NMR spectroscopy and mass spectrometry.
引用
收藏
页码：246 / 248
页数：3
相关论文
共 50 条
  • [21] Synthesis of Optically Pure 3R-methylcyclopentan-1-one from L-(-)-menthol
    G. Yu. Ishmuratov
    M. P. Yakovleva
    V. A. Ganieva
    G. R. Gareeva
    R. R. Muslukhov
    G. A. Tolstikov
    Chemistry of Natural Compounds, 2005, 41 : 549 - 551
  • [22] Synthesis of optically pure 3R-methylcyclopentan-1-one from L-(-)-menthol
    Ishmuratov, GY
    Yakovleva, MP
    Ganieva, VA
    Gareeva, GR
    Muslukhov, RR
    Tolstikov, GA
    CHEMISTRY OF NATURAL COMPOUNDS, 2005, 41 (05) : 549 - 551
  • [23] Stereoselective Synthesis of the Antileukemic Sesquiterpene (+)-Caparratriene from L-menthol and Tiglic Aldehyde
    Vydrina, V. A.
    Kravchenko, A. A.
    Yakovleva, M. P.
    Ishmuratova, N. M.
    Ishmuratov, G. Yu.
    CHEMISTRY OF NATURAL COMPOUNDS, 2018, 54 (03) : 461 - 463
  • [24] Synthesis of L-Menthol Oleate Catalyzed by Lipase Immobilized on Modified Macroporous Resins
    Li X.-Y.
    Zhou H.-Y.
    Zhou H.
    Wei P.
    Gao Xiao Hua Xue Gong Cheng Xue Bao/Journal of Chemical Engineering of Chinese Universities, 2018, 32 (05): : 1134 - 1139
  • [25] Synthesis of Amphiphilic Graphene Quantum Dots and Their Sustained Release Effect on L-Menthol
    Li, Ming
    Cui, Xiaoqian
    Wang, Xuan
    Li, Zaijun
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2020, 41 (02): : 324 - 330
  • [26] Stereoselective Synthesis of the Antileukemic Sesquiterpene (+)-Caparratriene from L-menthol and Tiglic Aldehyde
    V. A. Vydrina
    A. A. Kravchenko
    M. P. Yakovleva
    N. M. Ishmuratova
    G. Yu. Ishmuratov
    Chemistry of Natural Compounds, 2018, 54 : 461 - 463
  • [27] Synthesis of Dehydroabietane Sulfonamides Containing Amino Acid Ester and Hydrazide Fragments
    E. S. Izmest’ev
    D. V. Petukhov
    S. V. Pestova
    S. A. Rubtsova
    Russian Journal of Organic Chemistry, 2023, 59 : 67 - 77
  • [28] Synthesis of Dehydroabietane Sulfonamides Containing Amino Acid Ester and Hydrazide Fragments
    Izmest'ev, E. S.
    Petukhov, D. V.
    Pestova, S. V.
    Rubtsova, S. A.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2023, 59 (01) : 67 - 77
  • [29] Synthesis of enantiomerically pure macrolides with hydrazide fragments from tetrahydropyran and l-(+)-tartaric acid derivatives
    G. Yu. Ishmuratov
    M. P. Yakovleva
    G. R. Mingaleeva
    M. A. Shutova
    R. R. Muslukhov
    E. M. Vyrypaev
    A. G. Tolstikov
    Russian Chemical Bulletin, 2013, 62 : 217 - 219
  • [30] Synthesis of enantiomerically pure macrolides with hydrazide fragments from tetrahydropyran and L-(+)-tartaric acid derivatives
    Ishmuratov, G. Yu.
    Yakovleva, M. P.
    Mingaleeva, G. R.
    Shutova, M. A.
    Muslukhov, R. R.
    Vyrypaev, E. M.
    Tolstikov, A. G.
    RUSSIAN CHEMICAL BULLETIN, 2013, 62 (01) : 217 - 219
12345