Copper(<sc>i</sc>)-catalyzed coupling of alkynyl glycosides: synthesis of buta-1,3-diyne-linked disaccharides and dinucleosides

被引:0
|
作者
Banday, Junaid Shafi [1 ,2 ]
Ahmed, Sajjad [1 ,2 ]
Ahmed, Qazi Naveed [1 ,2 ]
机构
[1] CSIR Indian Inst Integrat Med, Nat Prod & Med Chem Div, Jammu 180001, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, India
关键词
POLYACETYLENES; CANCER;
D O I
暂无
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Herein we report copper-catalyzed coupling of alkynyl glycosides facilitating the synthesis of buta-1,3-diyne-linked disaccharides. The reaction is characterized by mild conditions employing eco-friendly reagents, resulting in good yields of the desired products. This methodology exhibits significant functional group tolerance with broad substrate scope. Furthermore, we have successfully extended this approach to the synthesis of buta-1,3-diyne-linked dinucleosides.
引用
收藏
页码:2615 / 2619
页数:5
相关论文
共 16 条
  • [1] Facile synthesis of 2-alkynyl buta-1,3-dienes via sonogashira cross-coupling methodology
    Shao, LX
    Shi, M
    JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (21): : 8635 - 8637
  • [2] Synthesis of antibacterial 1,3-diyne-linked peptoids from an Ugi-4CR/Glaser coupling approach
    Brauer, Martin C. N.
    Neves Filho, Ricardo A. W.
    Westermann, Bernhard
    Heinke, Ramona
    Wessjohann, Ludger A.
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2015, 11 : 1 - 6
  • [3] Copper(I) Iodide Catalyzed Cross-Coupling Reaction of Terminal Alkynes with 1-Bromoalkynes: A Simple Synthesis of Unsymmetrical Buta-1,3-diynes
    Wang, Shihua
    Yu, Lin
    Li, Pinhua
    Meng, Lingguo
    Wang, Lei
    SYNTHESIS-STUTTGART, 2011, (10): : 1541 - 1546
  • [4] Palladium(0)-catalyzed decarboxylation of buta-2,3-dienyl 2′-alkynoates:: Approach to the synthesis of 2-alkynyl buta-1,3-dienes
    Sim, So Hee
    Park, Hee-Jun
    Lee, Sang Ick
    Chung, Young Keun
    ORGANIC LETTERS, 2008, 10 (03) : 433 - 436
  • [5] Stereodivergent synthesis of 2-alkynyl buta-1,3-dienes using Sonogashira coupling with controllable retention or inversion of olefin geometry
    Shakhmaev, Rinat N.
    Ignatishina, Maria G.
    Zorin, Vladimir V.
    TETRAHEDRON LETTERS, 2020, 61 (10)
  • [6] Copper(I)-catalyzed reaction of diaryl buta-1,3-diynes with cyclic amines: an atom-economic approach to amino-substituted naphthalene derivatives
    Sun, Hongbin
    Wu, Xiaoli
    Hua, Ruimao
    TETRAHEDRON LETTERS, 2011, 52 (34) : 4408 - 4411
  • [7] Copper(I)-catalyzed three-component coupling leading to an efficient synthesis of β,γ-alkynyl α-amino acid derivatives
    Shao, Zhihui
    Chan, Albert S. C.
    SYNTHESIS-STUTTGART, 2008, (18): : 2868 - 2870
  • [8] Palladium-catalyzed carbocyclization-cross-coupling reactions of two different allenic moieties: synthesis of 3-(buta-1,3-dienyl) carbazoles and mechanistic insights
    Alcaide, Benito
    Almendros, Pedro
    Alonso, Jose M.
    Fernandez, Israel
    CHEMICAL COMMUNICATIONS, 2012, 48 (52) : 6604 - 6606
  • [9] Palladium-Catalyzed Cross-Coupling Reactions of 1,2-Diiodoalkenes with Terminal Alkynes: Selective Synthesis of Unsymmetrical Buta-1,3-diynes and 2-Ethynylbenzofurans
    Liang, Yun
    Tao, Li-Ming
    Zhang, Yue-Hua
    Li, Jin-Heng
    SYNTHESIS-STUTTGART, 2008, (24): : 3988 - 3994
  • [10] DFT investigation of Cu(<sc>i</sc>)-catalyzed addition of 1,4-pentadiene to acetophenone: mechanism and selectivity for the synthesis of a chiral tertiary alcohol with a 1,3-diene unit
    Xu, Jihong
    Yang, Yiying
    Liu, Chengbu
    Zhang, Dongju
    ORGANIC CHEMISTRY FRONTIERS, 2024, 11 (06): : 1748 - 1757