One-pot expeditious synthesis of glycosylated esters through activation of carboxylic acids using trichloroacetonitrile

被引:3
|
作者
Yadav, Mangal S. [1 ]
Jaiswal, Manoj K. [1 ]
Kumar, Sunil [1 ]
Singh, Sumit K. [1 ]
Ansari, Faisal J. [1 ]
Tiwari, Vinod K. [1 ]
机构
[1] Banaras Hindu Univ, Inst Sci, Dept Chem, Varanasi 221005, India
关键词
Alcohol; Carboxylic acid; Glycosylated ester; Trichloroacetimidate; CLICK CHEMISTRY; MIXED ANHYDRIDE; ESTERIFICATION; CATALYSTS; CARBONYLATION; AMIDATION; COMPLEXES; CLEAVAGE;
D O I
10.1016/j.carres.2022.108674
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Acetimidates, a valuable intermediate has been well explored as versatile synthon in a number of organic transformations particularly as suitable donors in glycosylation reactions. Herein, we explored acetimidates to furnish high-to-excellent yield of diverse glycosylated esters under one-pot mild reaction condition. The commercially available trichloroacetonitrile is implemented for the activation of carboxylic acid via in situ generation of trichloroacetimidate, which was subsequently attacked by sugar alcohols to deliver high-to -excellent yields of desired glycosylated esters. The devised method has some notable features such as metal -free condition, one-pot mild reaction condition, easy-handling, high-to-excellent yields, and broad substrate scope.
引用
收藏
页数:11
相关论文
共 50 条
  • [1] One-pot expeditious synthesis of glycosylated esters through activation of carboxylic acids using trichloroacetonitrile
    Yadav, Mangal S.
    Jaiswal, Manoj K.
    Kumar, Sunil
    Singh, Sumit K.
    Ansari, Faisal J.
    Tiwari, Vinod K.
    Carbohydrate Research, 2022, 521
  • [2] One-Pot Reaction of Carboxylic Acids and Ynol Ethers for The Synthesis of β-Keto Esters
    Zeng, Linwei
    Lai, Zhencheng
    Cui, Sunliang
    JOURNAL OF ORGANIC CHEMISTRY, 2018, 83 (23): : 14834 - 14841
  • [3] Use of pentafluorophenyl esters for one-pot protection activation of amino and thiol carboxylic acids
    Gayo, LM
    Suto, MJ
    TETRAHEDRON LETTERS, 1996, 37 (28) : 4915 - 4918
  • [4] One-pot synthesis of tetronic acids from esters
    Mallinger, Aurelie
    Le Gall, Thierry
    Mioskowski, Charles
    SYNLETT, 2008, (03) : 386 - 388
  • [5] A novel approach for the synthesis of β-keto esters: one-pot reaction of carboxylic acids with chlorosulfonyl isocyanate
    Atmaca, Ufuk
    ARKIVOC, 2020, : 220 - 227
  • [6] Synthesis of ketones from carboxylic acids using a convenient, one-pot protocol
    Shah, Unnati
    Rak, Jennifer
    Sivaram, Shobika
    Kwamboka, Roselyn
    Aslanian, Robert
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2014, 247
  • [7] Pyrazoles: 'one-pot' synthesis from arenes and carboxylic acids
    Kim, Jung Keun
    Gong, Ming
    Shokova, Elvira A.
    Tafeenko, Viktor A.
    Kovaleva, Olga, V
    Wu, Yangjie
    Kovalev, Vladimir V.
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2020, 18 (29) : 5625 - 5638
  • [8] One-Pot Reaction of Carboxylic Acids, Ynol Ethers, and m-CPBA for Synthesis of α-Carbonyloxy Esters
    Zeng, Linwei
    Sajiki, Hironao
    Cui, Sunliang
    ORGANIC LETTERS, 2019, 21 (16) : 6423 - 6426
  • [9] One-pot synthesis of amides from carboxylic acids activated using thionyl chloride
    Leggio, A.
    Belsito, E. L.
    De Luca, G.
    Di Gioia, M. L.
    Leotta, V.
    Romio, E.
    Siciliano, C.
    Liguori, A.
    RSC ADVANCES, 2016, 6 (41) : 34468 - 34475
  • [10] MILD, ONE-POT CONVERSION OF CARBOXYLIC-ACIDS INTO ESTERS USING PHASE-TRANSFER CATALYSIS
    PUNTAMBEKAR, HM
    NAIK, DG
    KAPADI, AH
    INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1993, 32 (07): : 793 - 794