Synthesis and NMR elucidation of four novel 2-(trimethylsilyl)ethyl glycosides

被引:2
|
作者
Qu, Huanhuan [1 ,2 ]
Sun, Wenji [2 ]
Zhang, Yanyan [1 ]
Sollogoub, Matthieu [1 ]
Zhang, Yongmin [1 ]
机构
[1] Univ Paris 06, CNRS, Inst Parisien Chim Mol, UMR 7201, F-75005 Paris, France
[2] NW Univ Xian, Biomed Key Lab Shaanxi Prov, Xian 710069, Peoples R China
关键词
Total synthesis; Structure elucidation; Glycosides; NMR spectroscopy; Oligosaccharides; CHEMICAL-SYNTHESIS; GLYCOSYLATION; OLIGOSACCHARIDES; TRANSFORMATION;
D O I
10.1007/s11164-013-1060-0
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Four novel 2-(trimethylsilyl)ethyl glycosides have been synthesized by a short and efficient route starting from d-glucose. Their structures were elucidated by applying high-resolution mass spectra, and one-dimensional and two-dimensional NMR techniques. These glycosides were prepared and used as intermediate building blocks in the scheme developed for oligosaccharide construction.
引用
收藏
页码:1557 / 1564
页数:8
相关论文
共 50 条
  • [1] Synthesis and NMR elucidation of four novel 2-(trimethylsilyl)ethyl glycosides
    Huanhuan Qu
    Wenji Sun
    Yanyan Zhang
    Matthieu Sollogoub
    Yongmin Zhang
    Research on Chemical Intermediates, 2014, 40 : 1557 - 1564
  • [2] Synthesis and characterization of four novel 2-(trimethylsilyl)ethyl glycosides
    Qu, Huanhuan
    Sun, Wenji
    Sun, Tao
    Sollogoub, Matthieu
    Zhang, Yongmin
    RESEARCH ON CHEMICAL INTERMEDIATES, 2015, 41 (02) : 1107 - 1113
  • [3] Synthesis and characterization of four novel 2-(trimethylsilyl)ethyl glycosides
    Huanhuan Qu
    Wenji Sun
    Tao Sun
    Matthieu Sollogoub
    Yongmin Zhang
    Research on Chemical Intermediates, 2015, 41 : 1107 - 1113
  • [4] Synthesis of 2-(trimethylsilyl)ethyl α-D-mannopyranosides revisited
    Saksena, R
    Zhang, J
    Kovác, P
    JOURNAL OF CARBOHYDRATE CHEMISTRY, 2002, 21 (06) : 453 - 470
  • [5] Synthesis and NMR elucidation of novel pentacycloundecane-based peptides
    Altaib, Mohamed S.
    Arvidsson, Per I.
    Govender, Thavendran
    Maguire, Glenn E. M.
    Makatini, Maya
    Onajole, Oluseye K.
    Kruger, Hendrik G.
    MAGNETIC RESONANCE IN CHEMISTRY, 2010, 48 (06) : 435 - 442
  • [6] Synthesis and NMR Spectroscopic Elucidation of Four Diastereoisomers of Oxygenated Bisabolane Side Chain
    Hirai, Misaki
    Miyazaki, Rurina
    Mitsui, Kana
    Kiuchi, Kota
    Onuki, Hiroyuki
    Hirota, Hiroshi
    Kuroda, Chiaki
    HELVETICA CHIMICA ACTA, 2015, 98 (08) : 1035 - 1060
  • [7] Straightforward Synthesis of Novel 1-(2′-α-O-D-Glucopyranosyl ethyl) 2-Arylbenzimidazoles
    Arumugam, Natarajan
    Rahim, Aisyah Saad Abdul
    Abd Hamid, Shafida
    Osman, Hasnah
    MOLECULES, 2012, 17 (08) : 9887 - 9899
  • [8] Direct Synthesis of 2,6-Dideoxy-β-glycosides and β-Rhamnosides with a Stereodirecting 2-(Diphenylphosphinoyl)acetyl Group
    Liu, Xianglai
    Lin, Yetong
    Peng, Wenyi
    Zhang, Zhaolun
    Gao, Longwei
    Zhou, Yueer
    Song, Zhe
    Wang, Yingjie
    Xu, Peng
    Yu, Biao
    Sun, Haopeng
    Xie, Weijia
    Li, Wei
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2022, 61 (33)
  • [9] Novel stereoelectronic behavior of bicyclic glycosyl donors:: Application to the synthesis of both 2-deoxy-α- and -β-glycosides
    Dios, A
    Nativi, C
    Capozzi, G
    Franck, RW
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1999, 1999 (08) : 1869 - 1874
  • [10] Total synthesis of 2-(5,6-epoxyisoprostane A2)phosphorylcholine and elucidation of the relative configuration of the isoprostane moiety
    Acharya, HP
    Kobayashi, Y
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (22) : 3481 - 3484