Palladium(ii)-catalyzed stereoselective synthesis of: C-glycosides from glycals with diaryliodonium salts

被引:0
|
作者
Pal, Kumar Bhaskar [1 ]
Lee, Jiande [1 ,2 ]
Das, Mrinmoy [1 ]
Liu, Xue-Wei [1 ]
机构
[1] Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, 21 Nanyang Link, Singapore,637371, Singapore
[2] Nanyang Environment and Water Research Institute, Nanyang Technological University 1 Cleantech Loop, Singapore,637141, Singapore
来源
Organic and Biomolecular Chemistry | 2020年 / 18卷 / 12期
基金
新加坡国家研究基金会;
关键词
Sugars - Palladium compounds - Salts - Glycosylation;
D O I
暂无
中图分类号
学科分类号
摘要
An efficient palladium(ii) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-Aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of glycals, including d-glucal, d-galactal, d-Allal, l-rhamnal, l-fucal, l-Arabinal, d-maltal, and d-lactal, occurred effectively and the corresponding C-glycosides were obtained in moderate to good yields. This protocol is commended as a significant addition to the field of carbohydrate chemistry due to the rich functional group compatibility, broad range of substrate scope and exceptional α-stereoselectivity. This journal is © The Royal Society of Chemistry.
引用
收藏
页码:2242 / 2251
相关论文
共 50 条
  • [21] Stereoselective Synthesis of C,C-Glycosides from exo-Glycals Enabled by Iron-Mediated Hydrogen Atom Transfer
    Tardieu, Damien
    Desnoyers, Marine
    Laye, Claire
    Hazelard, Damien
    Kern, Nicolas
    Compain, Philippe
    ORGANIC LETTERS, 2019, 21 (18) : 7262 - 7267
  • [22] Stereoselective Synthesis of 2-(β-C-Glycosyl)glycals: Access to Unusual β-C-Glycosides from 3-Deoxyglycals
    Reddy, Gadi Madhusudhan
    Rao, Boddu Uma Maheswara
    Sridhar, Perali Ramu
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (07): : 2782 - 2793
  • [23] HIGHLY STEREOSELECTIVE SYNTHESIS OF ARYL C-GLYCOSIDES
    蔡孟深
    邱东旭
    ChineseScienceBulletin, 1990, (07) : 615 - 616
  • [24] HIGHLY STEREOSELECTIVE SYNTHESIS OF ARYL C-GLYCOSIDES
    CAI, MS
    QIU, DX
    CHINESE SCIENCE BULLETIN, 1990, 35 (07): : 615 - 616
  • [25] STEREOSELECTIVE SYNTHESIS OF C-GLYCOSIDES WITH A GLYCOSYL DIANION
    WITTMAN, V
    KESSLER, H
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1993, 32 (07): : 1091 - 1093
  • [26] Synthesis of C-glycosides by Ti-catalyzed stereoselective glycosyl radical functionalization
    Jiang, Yi
    Wang, Quanquan
    Zhang, Xinglong
    Koh, Ming Joo
    CHEM, 2021, 7 (12): : 3377 - 3392
  • [27] Synthesis of C-glycosides from glycals or vinylogous lactones and trimethylsilyl ketene acetals
    Csuk, R
    Schaade, M
    Krieger, C
    TETRAHEDRON, 1996, 52 (18) : 6397 - 6408
  • [28] Copper mediated stereoselective synthesis of C-glycosides from unactivated alkynes
    Kusunuru, Anil Kumar
    Tatina, Madhubabu
    Yousuf, Syed Khalid
    Mukherjee, Debaraj
    CHEMICAL COMMUNICATIONS, 2013, 49 (86) : 10154 - 10156
  • [29] Stereoselective and site-divergent synthesis of C-glycosides
    Ping, Yuanyuan
    Kong, Wangqing
    CHINESE SCIENCE BULLETIN-CHINESE, 2024, 69 (32): : 4651 - 4653
  • [30] Stereoselective synthesis of α-C-glycosides of N-acetylgalactosamine
    Cipolla, L
    La Ferla, B
    Lay, L
    Peri, F
    Nicotra, F
    TETRAHEDRON-ASYMMETRY, 2000, 11 (01) : 295 - 303