Citation: Wu Qing-Kun, Li Yi-Xian, Jia Yue-Mei, Yu Chu-Yi. Synthesis of a novel C-branched polyhydroxylated cyclic nitrone[J]. Chinese Chemical Letters, ;2017, 28(4): 909-912. doi: 10.1016/j.cclet.2016.12.033 shu

Synthesis of a novel C-branched polyhydroxylated cyclic nitrone

Wu Qing-Kun ^a,b ,
Li Yi-Xian ^a ,
Jia Yue-Mei ^a ,
Yu Chu-Yi ^a,c,,

a.
Beijing National Laboratory for Molecular Science(BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China
b.
University of Chinese Academy of Sciences, Beijing 100049, China
c.
National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, China

Corresponding author: Yu Chu-Yi, yucy@iccas.ac.cn
Received Date: 14 November 2016
Revised Date: 8 December 2016
Accepted Date: 8 December 2016
Available Online: 10 April 2017

Figures(5)

A novel C-branched polyhydroxylated cyclic nitrone 25, which could be a valuable intermediate for the synthesis of C-branched pyrrolidine iminosugars, was synthesized starting from the commercially available L-arabinose in 29.0% total yield.
- Cyclic nitrone,
- Branched chain,
- Iminosugars,
- Azasugars,
- Polyhydroxylated pyrrolidine
1. [1]
  Asano N., Nash R.J., Molyneux R.J., Fleet G.W.J. Sugar-mimic glycosidase inhibitors:natural occurrence biological activity and prospects for therapeutic application[J]. Tetrahedron:Asymmetry, 2000,11:1645-1680. doi: 10.1016/S0957-4166(00)00113-0
2. [2]
  Watson A.A., Fleet G.W.J., Asano N., Molyneux R.J., Nash R.J. Polyhydroxylated alkaloids-natural occurrence and therapeutic applications[J]. Phytochemistry, 2001,56:265-295. doi: 10.1016/S0031-9422(00)00451-9
3. [3]
  Decroocq C., Stauffert F., Pamlard O.. Iminosugars as a new class of cholinesterase inhibitors[J]. Bioorg.Med.Chem.Lett., 2015,25:830-833. doi: 10.1016/j.bmcl.2014.12.071
4. [4]
  Chen H., Hao L., Zhu M.. Synthesis of bi-/tricyclic azasugars fused thiazinan-4-one and their HIV-RT inhibitory activity[J]. Bioorg.Med.Chem.Lett., 2014,24:3426-3429. doi: 10.1016/j.bmcl.2014.05.079
5. [5]
  Lahiri R., Ansari A.A., Vankar Y.D. Recent developments in design and synthesis of bicyclic azasugars, carbasugars and related molecules as glycosidase inhibitors[J]. Chem.Soc.Rev., 2013,42:5102-5118. doi: 10.1039/c3cs35525j
6. [6]
  Hill C.H., Viuff A.H., Spratley S.J.. Azasugar inhibitors as pharmacological chaperones for Krabbe disease[J]. Chem.Sci., 2015,6:3075-3086. doi: 10.1039/C5SC00754B
7. [7]
  Li Q., Ye X.S. Iminosugars as immunomodulating agents:synthesis and biological activities of 1-deoxynojirimycin and related compounds[J]. Isr.J. Chem., 2015,55:336-346. doi: 10.1002/ijch.v55.3/4
8. [8]
  Takahata H. Synthetic medicinal chemistry of the biomolecular components mimics[J]. Yakugaku Zasshi, 2013,133:575-585. doi: 10.1248/yakushi.13-00054
9. [9]
  Takahata H. Chiral synthesis of iminosugars[J]. Heterocycles, 2012,85:1351-1376. doi: 10.3987/REV-12-734
10. [10]
  Concia A.L., Gomez L., Parella T., Joglar J., Clapes P. Casuarine stereoisomers from achiral substrates:chemoenzymatic synthesis and inhibitory properties[J]. J.Org.Chem., 2014,79:5386-5389. doi: 10.1021/jo500991p
11. [11]
  Lin C.K., Cheng L.W., Li H.Y., Yun W.Y., Cheng W.C. Synthesis of novel polyhydroxylated pyrrolidine-triazole/-isoxazole hybrid molecules[J]. Org. Biomol.Chem., 2015,13:2100-2107. doi: 10.1039/C4OB01934B
12. [12]
  Si C.M., Mao Z.Y., Dong H.Q.. Divergent method to trans-5-hydroxy-6-alkynyl/alkenyl-2-piperidinones:syntheses of (-)-epiquinamide and (+)-swainsonine[J]. J.Org.Chem., 2015,80:5824-5833. doi: 10.1021/acs.joc.5b00803
13. [13]
  Martella D., D'Adamio G., Parmeggiani C.. Cycloadditions of sugar-derived nitrones targeting polyhydroxylated indolizidines[J]. Eur.J.Org.Chem., 2016:1588-1598.
14. [14]
  Soluch M., Grzeszczyk B., Staszewska-Krajewska O., Chmielewski M., Furman B.. Synthesis of thienamycin methyl ester from 2-deoxy-D-ribose via Kinugasa reaction[J]. J.Antibiot., 2016,69:164-168. doi: 10.1038/ja.2015.108
15. [15]
  Boisson J., Thomasset A., Racine E.. Hydroxymethyl-branched polyhydroxylated indolizidines:novel selective a-glucosidase inhibitors[J]. Org.Lett., 2015,17:3662-3665. doi: 10.1021/acs.orglett.5b01505
16. [16]
  Song Y.Y., Kinami K., Kato A.. First total synthesis of(+)-broussonetine W: glycosidase inhibition of natural product&analogs[J]. Org.Biomol.Chem., 2016,14:5157-5174. doi: 10.1039/C6OB00720A
17. [17]
  Qian B.C., Kamori A., Kinami K.. Epimerization of C5 of an N-hydroxypyrrolidine in the synthesis of swainsonine related iminosugars[J]. Org. Biomol.Chem., 2016,14:4488-4498. doi: 10.1039/C6OB00531D
18. [18]
  Li Y.X., Iwaki R., Kato A.. Fluorinated radicamine A and B:synthesis and glycosidase inhibition[J]. Eur.J.Org.Chem., 2016:1429-1438.
19. [19]
  Zhu J.S., Nakagawa S., Chen W.. Synthesis of eight stereoisomers of pochonicine:nanomolar inhibition of beta-N-acetylhexosaminidases[J]. J.Org. Chem., 2013,78:10298-10309. doi: 10.1021/jo401694e
20. [20]
  Zhang W., Sato K., Kato A.. Synthesis of fully substituted polyhydroxylated pyrrolizidines via cope-house cyclization[J]. Org.Lett, 2011,13:4414-4417. doi: 10.1021/ol201749c
21. [21]
  Best D., Jenkinson S.F., Saville A.W.. Cystic fibrosis and diabetes:isoLAB and isoDAB enantiomeric carbon-branched pyrrolidine iminosugars[J]. Tetrahedron Lett., 2010,51:4170-4174. doi: 10.1016/j.tetlet.2010.05.131
22. [22]
  Cruz F.P.d., Newberry S., Jenkinson S.F.. 4-C-Me-DAB and 4-C-Me-LAB— enantiomeric alkyl-branched pyrrolidine iminosugars—are specific and potent a-glucosidase inhibitors; acetone as the sole protecting group[J]. Tetrahedron Lett., 2011,52:219-223. doi: 10.1016/j.tetlet.2010.10.173
23. [23]
  Pawar N.J., Parihar V.S., Chavan S.T.. α-Geminal dihydroxymethyl piperidine and pyrrolidine iminosugars:synthesis, conformational analysis, glycosidase inhibitory activity, and molecular docking studies[J]. J.Org.Chem., 2012,77:7873-7882. doi: 10.1021/jo3009534
24. [24]
  Jenkinson S.F., Best D., Saville A.W.. C-branched iminosugars:alpha-glucosidase inhibition by enantiomers of isoDMDP, isoDGDP, and isoDAB-L-isoDMDP compared to miglitol and miglustat[J]. J.Org.Chem., 2013,78:7380-7397. doi: 10.1021/jo4005487
25. [25]
  Cren S., Wilson C., Thomas N.R. A rapid synthesis of hexofuranose-like iminosugars using ring-closing metathesis[J]. Org.Lett., 2005,7:3521-3523. doi: 10.1021/ol051232b
26. [26]
  Li H., Zhang Y., Favre S.. Synthesis of branched seven-membered 1-N-iminosugars and their evaluation as glycosidase inhibitors[J]. Carbohydr.Res., 2012,356:110-114. doi: 10.1016/j.carres.2011.10.039
27. [27]
  Zhang E., Bai P.Y., Sun W.. Synthesis and glycosidase inhibition evaluation of(3S, 4S)-3-((R)-1, 2-dihydroxyethyl)pyrrolidine-3, 4-diol[J]. Carbohydr.Res., 2016,434:33-36. doi: 10.1016/j.carres.2016.08.003
28. [28]
  F.León , Brouard I., Rivera A.. Isolation, structure elucidation, total synthesis, and evaluation of new natural and synthetic ceramides on human SK-MEL-1 melanoma cells[J]. J.Med.Chem., 2006,49:5830-5839. doi: 10.1021/jm0605334
29. [29]
  Wang W.B., Huang M.H., Li Y.X.. A practical synthesis of sugar-derived cyclic nitrones:powerful synthons for the synthesis of iminosugars[J]. Synlett, 2010:488-492.
1. [1]
  Yifei Zhang , Yuncong Xue , Laiwei Gao , Rui Liao , Feng Wang , Fei Wang . Merging non-covalent and covalent crosslinking: En route to single chain nanoparticles. Chinese Chemical Letters, 2024, 35(6): 109217-. doi: 10.1016/j.cclet.2023.109217
2. [2]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
3. [3]
  Yi Liu , Peng Lei , Yang Feng , Shiwei Fu , Xiaoqing Liu , Siqi Zhang , Bin Tu , Chen Chen , Yifan Li , Lei Wang , Qing-Dao Zeng . Topologically engineering of π-conjugated macrocycles: Tunable emission and photochemical reaction toward multi-cyclic polymers. Chinese Chemical Letters, 2024, 35(10): 109571-. doi: 10.1016/j.cclet.2024.109571
4. [4]
  Shulei Hu , Yu Zhang , Xiong Xie , Luhan Li , Kaixian Chen , Hong Liu , Jiang Wang . Rh(Ⅲ)-catalyzed late-stage C-H alkenylation and macrolactamization for the synthesis of cyclic peptides with unique Trp(C7)-alkene crosslinks. Chinese Chemical Letters, 2024, 35(8): 109408-. doi: 10.1016/j.cclet.2023.109408
5. [5]
  Ke Zhang , Sheng Zuo , Pengyuan You , Tong Ru , Fen-Er Chen . Palladium-catalyzed stereoselective decarboxylative [4 + 2] cyclization of 2-methylidenetrimethylene carbonates with pyrrolidone-derived enones: Straightforward access to chiral tetrahydropyran-fused spiro-pyrrolidine-2,3-diones. Chinese Chemical Letters, 2024, 35(6): 109157-. doi: 10.1016/j.cclet.2023.109157
6. [6]
  Zhili Li , Qijun Wo , Dongdong Huang , Dezhong Zhou , Lei Guo , Yeqing Mao . Improving gene transfection efficiency of highly branched poly(β-amino ester)s through the in-situ conversion of inactive terminal groups. Chinese Chemical Letters, 2024, 35(8): 109737-. doi: 10.1016/j.cclet.2024.109737
7. [7]
  Fei Yin , Erli Yang , Xue Ge , Qian Sun , Fan Mo , Guoqiu Wu , Yanfei Shen . Coupling WO₃₋_x dots-encapsulated metal-organic frameworks and template-free branched polymerization for dual signal-amplified electrochemiluminescence biosensing. Chinese Chemical Letters, 2024, 35(4): 108753-. doi: 10.1016/j.cclet.2023.108753
8. [8]
  Xinyu Yu , Fei Wu , Xianglang Sun , Linna Zhu , Baoyu Xia , Zhong'an Li . Low-cost dopant-free fluoranthene-based branched hole transporting materials for efficient and stable n-i-p perovskite solar cells. Chinese Chemical Letters, 2024, 35(10): 109821-. doi: 10.1016/j.cclet.2024.109821

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(584)
HTML views(21)

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