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
  • [31] DES-Based Biocatalysis as a Green Alternative for the l-menthyl Ester Production Based on l-menthol Acylation
    Ion, Sabina
    Olanescu, Florentina
    Teodorescu, Florina
    Tincu, Robert
    Gheorghe, Daniela
    Parvulescu, Vasile, I
    Tudorache, Madalina
    MOLECULES, 2022, 27 (16):
  • [32] Kinetic resolution of citronellal by chiral aluminum catalysts: L-menthol synthesis from citral
    Itoh, Hisanori
    Maeda, Hironori
    Yamada, Shinya
    Hori, Yoji
    Mino, Takashi
    Sakamoto, Masami
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (09): : 1107 - 1115
  • [33] Synthesis and properties of chiral dopants synthesized on the base of 2-methylbutanol and l-menthol
    Kozachenko, A.
    Nazarenko, V.
    Sorokin, V.
    Tishchenko, V.
    Tishchenko, Yu.
    Vakhnin, S.
    Molecular Crystals and Liquid Crystals Science and Technology Section A: Molecular Crystals and Liquid Crystals, 1998, 324 : 251 - 256
  • [34] Synthesis of L-menthyl isovalerate by esterification of isovaleric acid with L-menthol under microwave irradiation
    Kh. A. Suerbaev
    N. Zh. Kudaibergenov
    N. O. Appazov
    G. Zh. Zhaksylykova
    Russian Journal of Organic Chemistry, 2016, 52 : 585 - 586
  • [35] Highly selective aluminium-catalysed intramolecular Prins reaction for L-menthol synthesis
    Itoh, H.
    Maeda, H.
    Yamada, S.
    Hori, Y.
    Mino, T.
    Sakamoto, Masami
    RSC ADVANCES, 2014, 4 (106): : 61619 - 61623
  • [36] Synthesis of L-menthyl isovalerate by esterification of isovaleric acid with L-menthol under microwave irradiation
    Suerbaev, Kh. A.
    Kudaibergenov, N. Zh.
    Appazov, N. O.
    Zhaksylykova, G. Zh.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2016, 52 (04) : 585 - 586
  • [37] Undec-10-enoic Acid in the Synthesis of Macroheterocycles Containing Hydrazide and Ester Fragments
    G. R. Mingaleeva
    M. P. Yakovleva
    R. R. Salakhutdinov
    A. G. Tolstikov
    G. Yu. Ishmuratov
    Russian Journal of Organic Chemistry, 2019, 55 : 514 - 517
  • [38] Undec-10-enoic Acid in the Synthesis of Macroheterocycles Containing Hydrazide and Ester Fragments
    Mingaleeva, G. R.
    Yakovleva, M. P.
    Salakhutdinov, R. R.
    Tolstikov, A. G.
    Ishmuratov, G. Yu.
    RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2019, 55 (04) : 514 - 517
  • [39] Synthesis of L-menthol lactate using acidic ionic liquid [Hnmp]+ HSO4- as catalyst
    张爱华
    肖志红
    刘汝宽
    张良波
    李培旺
    李力
    湖南林业科技, 2011, (04) : 8 - 11
  • [40] Synthesis from (+)-α-pinene of optically active macrocycles containing cyclobutane, ester, azine, or hydrazide groups
    G. Yu. Ishmuratov
    G. R. Mingaleeva
    O. O. Shakhanova
    R. R. Muslukhov
    M. P. Yakovleva
    L. P. Botsman
    A. G. Tolstikov
    Chemistry of Natural Compounds, 2011, 47 : 210 - 214