Home

Citation: Zhang Pingzhu, Liu Huan, Wei Xiao, Ma Chen, Wang Qiwei, Li Xiaoliu. Synthesis of C-Glycosides Ribosyl-Acid and Ribosyl-Aldehyde[J]. Chinese Journal of Organic Chemistry, ;2016, 36(7): 1690-1695. doi: 10.6023/cjoc201602003 shu

Synthesis of C-Glycosides Ribosyl-Acid and Ribosyl-Aldehyde

1.
Key Laboratory of Chemical Biology of Hebei Province, School of Chemistry and Environmental Science, Hebei University, Baoding 071002

Corresponding author: Li Xiaoliu,
Received Date: 1 February 2016
Revised Date: 9 March 2016

Fund Project: the National Natural Science Foundation of China 21172051the National Natural Science Foundation of China 21372059

Figures(4)

For exploring a simple and efficient synthetic method of C-glycosides, (2, 3-O-isopropylidene)-β-C-D-ribosyl ethyl acetate and (2, 3-O-isopropylidene)-β-C-D-ribosyl acetic acid were stereospecifically synthesized by a one-pot tandem Wittig-Michael addition reaction, and then treated with corresponding base, respectively. The acetates were reduced by DIBAL-H to obtain the corresponding glycosyl aldehyde. D-xylose was treated following the procedure of acetonide of 1, 2-position, trifluoroacetoxyation of 3, 5-position. The trifluoroacetoxyl groups were substituted by azido groups, followed by the one-pot tandem Wittig-Michael addition reaction, and then treated with corresponding base. 3, 5-Diazido-β-C-D-ribosyl acetic acid was obtained in high stereo specificity.
- C-glycosides,
- Wittig-Michael addition,
- ribosyl-acid,
- aldehyde,
- azides
1. [1]
  Varki, A.; Cummings, R.; Esko, J.; Freeze, H.; Hart, G.; Marth, J. Essentials of Glycobiology, Lajolla, California, 2002, p. 57. (b) Science, 2001, 291(5512), the all articles. (c) Nature, 2007, 446(7139), the all articles.
2. [2]
  Fraser-Reid, B. O.; Tatsuta, K.; Them, J. Glycoscience: Chemistry and Chemical Biology, 2nd ed., Springer, Berlin, 2008. (b) Wong, C. H. Carbohydrate-based Drug Discovery, WILEY-VCH, Weinheim, 2003.
3. [3]
  Zou, W. Curr. Top. Med. Chem. 2005, 5(14), 1297. (b) Wang, J.; Kovác, P.; Sinäy, P.; Glaudemans, P. J. Carbohydr. Res. 1998, 308, 191.
4. [4]
  Lalithaa, K.; Muthusamya, K.; Siva Prasada, Y.; Vemulab, P. K.; Nagarajana, S. Carbohydr. Res. 2015, 402, 158. (b) Clercq, E. D. J. Med. Chem. 2016, 59, 2301.(c) Hocek, M.; Pavel, K.; Stambaský, J. Chem. Rev. 2009, 109, 6729. (d) Moos, E. v.; Ben, R. N. Curr. Top. Med. Chem. 2005, 5(14), 1351.
5. [5]
  Postema, M. H. D. Tetrahedron 1992, 48, 8545. (b) Liu, L.; McKee, M.; Postema, M. H. D. Curr. Org. Chem. 2001, 5, 1133.
6. [6]
  von Itzstein, M.; Taylor, N. R. J. Med. Chem. 1994, 37, 616.
7. [7]
  Ma, D. L.; Li, X. L.; Hao, L.; Zhang, P. Z.; Chen, h.; Zhao, Y. Chem. J. Chin. Univ. 2014, 355, 959 (in Chinese). (马东来, 李小六, 郝乐, 张平竹, 陈华, 赵影, 高等学校化学学报, 2014, 355, 959.)
1. [1]
  Hao Wu , Zhen Liu , Dachang Bai . ¹H NMR Spectrum of Amide Compounds. University Chemistry, 2024, 39(3): 231-238. doi: 10.3866/PKU.DXHX202309020
2. [2]
  Qianlang Wang , Jijun Sun , Qian Chen , Quanqin Zhao , Baojuan Xi . The Appeal of Organophosphorus Compounds: Clearing Their Name. University Chemistry, 2025, 40(4): 299-306. doi: 10.12461/PKU.DXHX202405205
3. [3]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016
4. [4]
  Ying Xiong , Guangao Yu , Lin Wu , Qingwen Liu , Houjin Li , Shuanglian Cai , Zhanxiang Liu , Xingwen Sun , Yuan Zheng , Jie Han , Xin Du , Chengshan Yuan , Qihan Zhang , Jianrong Zhang , Shuyong Zhang . Basic Operations and Specification Suggestions for Determination of Physical Constants of Organic Compounds. University Chemistry, 2025, 40(5): 106-121. doi: 10.12461/PKU.DXHX202503079
5. [5]
  Yongjian Zhang , Fangling Gao , Hong Yan , Keyin Ye . Electrochemical Transformation of Organosulfur Compounds. University Chemistry, 2025, 40(5): 311-317. doi: 10.12461/PKU.DXHX202407035
6. [6]
  Geyang Song , Dong Xue , Gang Li . Recent Advances in Transition Metal-Catalyzed Synthesis of Anilines from Aryl Halides. University Chemistry, 2024, 39(2): 321-329. doi: 10.3866/PKU.DXHX202308030
7. [7]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
8. [8]
  Aidang Lu , Yunting Liu , Yanjun Jiang . Comprehensive Organic Chemistry Experiment: Synthesis and Characterization of Triazolopyrimidine Compounds. University Chemistry, 2024, 39(8): 241-246. doi: 10.3866/PKU.DXHX202401029
9. [9]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
10. [10]
  Xiaofeng Zhu , Bingbing Xiao , Jiaxin Su , Shuai Wang , Qingran Zhang , Jun Wang . Transition Metal Oxides/Chalcogenides for Electrochemical Oxygen Reduction into Hydrogen Peroxides. Acta Physico-Chimica Sinica, 2024, 40(12): 2407005-. doi: 10.3866/PKU.WHXB202407005
11. [11]
  Jinfeng Chu , Lan Jin , Yu-Fei Song . Exploration and Practice of Flipped Classroom in Inorganic Chemistry Experiment: a Case Study on the Preparation of Inorganic Crystalline Compounds. University Chemistry, 2024, 39(2): 248-254. doi: 10.3866/PKU.DXHX202308016
12. [12]
  Zhen Yao , Bing Lin , Youping Tian , Tao Li , Wenhui Zhang , Xiongwei Liu , Wude Yang . Visible-Light-Mediated One-Pot Synthesis of Secondary Amines and Mechanistic Exploration. University Chemistry, 2024, 39(5): 201-208. doi: 10.3866/PKU.DXHX202311033
13. [13]
  Zhuoming Liang , Ming Chen , Zhiwen Zheng , Kai Chen . Multidimensional Studies on Ketone-Enol Tautomerism of 1,3-Diketones By ¹H NMR. University Chemistry, 2024, 39(7): 361-367. doi: 10.3866/PKU.DXHX202311029
14. [14]
  Yanan Liu , Yufei He , Dianqing Li . Preparation of Highly Dispersed LDHs-based Catalysts and Testing of Nitro Compound Reduction Performance: A Comprehensive Chemical Experiment for Research Transformation. University Chemistry, 2024, 39(8): 306-313. doi: 10.3866/PKU.DXHX202401081
15. [15]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
16. [16]
  Feng Han , Fuxian Wan , Ying Li , Congcong Zhang , Yuanhong Zhang , Chengxia Miao . Comprehensive Organic Chemistry Experiment: Phosphotungstic Acid-Catalyzed Direct Conversion of Triphenylmethanol for the Synthesis of Oxime Ethers. University Chemistry, 2025, 40(3): 342-348. doi: 10.12461/PKU.DXHX202405181
17. [17]
  Yueguang Chen , Wenqiang Sun . “Carbon” Adventures. University Chemistry, 2024, 39(9): 248-253. doi: 10.3866/PKU.DXHX202308074
18. [18]
  Jinyi Sun , Lin Ma , Yanjie Xi , Jing Wang . Preparation and Electrocatalytic Nitrogen Reduction Performance Study of Vanadium Nitride@Nitrogen-Doped Carbon Composite Nanomaterials: A Recommended Comprehensive Chemistry Experiment. University Chemistry, 2024, 39(4): 184-191. doi: 10.3866/PKU.DXHX202310094
19. [19]
  Yihao Zhao , Jitian Rao , Jie Han . Synthesis and Photochromic Properties of 3,3-Diphenyl-3H-Naphthopyran: Design and Teaching Practice of a Comprehensive Organic Experiment. University Chemistry, 2024, 39(10): 149-155. doi: 10.3866/PKU.DXHX202402050
20. [20]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(826)
HTML views(97)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Address：Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888

DownLoad: Full-Size Img PowerPoint

Return