Synthesis of C-spiro-glycoconjugates from sugar lactones via zinc mediated Barbier reaction

被引：27
作者：
Lambu, Mallikharjuna Rao [1 ,2 ]
Hussain, Altaf [1 ,2 ]
Sharma, Deepak K. [1 ,2 ]
Yousuf, Syed Khalid [3 ]
Singh, Baldev [2 ]
Tripathi, Anil. K. [2 ]
Mukherjee, Debaraj [1 ,2 ]
机构：
[1] Acad Sci & Innovat Res, New Delhi, India
[2] CSIR Indian Inst Integrat Med, NPC Microbes, Jammu 180001, J&K, India
[3] CSIR Indian Inst Integrat Med, Med Chem Div, Srinagar 190005, Jammu & Kashmir, India
来源：
RSC ADVANCES | 2014年 / 4卷 / 22期
关键词：
STEREOSELECTIVE-SYNTHESIS; GEM-BISALLYLATION; GLYCOSIDES; PROPARGYLATION; CYCLOADDITION; DERIVATIVES; ALDEHYDES; POTENT; INDIUM; MILD;
D O I：
10.1039/c3ra46796a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Anomeric gem-diallylation, mono-beta-crotylation and mono-beta-propargylation of sugar 1,5 and 1,4 lactones have been achieved under Barbier reaction conditions using Zn powder and a catalytic amount of TMSCl as an activator. Ring closing olefin metathesis of the synthesized gem-diallyl derivatives furnished C-spiro cyclopentene glycosides. Finally, the cyclopentene rings were converted into carbohydrate based tricyclic morpholine fused triazole glycoconjugates as potential SGLT2 inhibitors.
引用
收藏
页码：11023 / 11028
页数：6
相关论文
共 51 条
  • [1] Akira H., 1984, TETRAHEDRON LETT, V25, P2383
  • [2] Akira H., 1987, CARBOHYD RES, V171, P223
  • [3] DIMETHYL SULFOXIDE-ACID ANHYDRIDE MIXTURES . NEW REAGENTS FOR OXIDATION OF ALCOHOLS
    ALBRIGHT, JD
    GOLDMAN, L
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1965, 87 (18) : 4214 - +
  • [4] Sugar-Based Enantiomeric and Conformationally Constrained Pyrrolo[2,1-c][1,4]-Benzodiazepines as Potential GABAA Ligands
    Araujo, Ana C.
    Rauter, Amelia P.
    Nicotra, Francesco
    Airoldi, Cristina
    Costa, Barbara
    Cipolla, Laura
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2011, 54 (05) : 1266 - 1275
  • [5] A facile synthesis of flumazenil analogues
    Broggini, G
    Molteni, G
    Terraneo, A
    Zecchi, G
    [J]. TETRAHEDRON, 1999, 55 (51) : 14803 - 14806
  • [6] Chen GR, 2001, EUR J ORG CHEM, V2001, P2939, DOI 10.1002/1099-0690(200108)2001:15<2939::AID-EJOC2939>3.0.CO
  • [7] 2-H
  • [8] Indium and zinc mediated Barbier type reactions: Allylation and propargylation reactions of 6-oxopenicillanate and 7-oxocephalosporanate
    Cho, YS
    Lee, JE
    Pae, AN
    Choi, KI
    Koh, HY
    [J]. TETRAHEDRON LETTERS, 1999, 40 (09) : 1725 - 1728
  • [9] Corey EJ, 1998, ANGEW CHEM INT EDIT, V37, P388, DOI 10.1002/(SICI)1521-3773(19980302)37:4<388::AID-ANIE388>3.0.CO
  • [10] 2-V
123456