Syntheses of Azasugar Intermediates Containing Aldehyde Group or Azide Group

doi:10.6023/cjoc201203008

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (9): 1708-1714.DOI: 10.6023/cjoc201203008 Previous Articles Next Articles

Articles

含醛基及叠氮基氮杂糖中间体的合成

李小六, 魏思楠, 张宏波, 张平竹, 王玮, 陈华

河北大学化学与环境科学学院河北省化学生物学重点实验室保定 071002

收稿日期:2012-03-26 修回日期:2012-05-16 发布日期:2012-05-09
通讯作者: 李小六, 陈华 E-mail:lixl@hbu.cn, hua-todd@hbu.cn
基金资助:
国家自然科学基金(Nos.20972039, 21172051)、河北省自然科学基金石药集团医药联合基金(Nos.B2011201169, B2012201113)、河北省教育厅自然科学基金(Nos.ZH2011110, Y2011119)资助项目

Syntheses of Azasugar Intermediates Containing Aldehyde Group or Azide Group

Li Xiaoliu, Wei Sinan, Zhang Hongbo, Zhang Pingzhu, Wang Wei, Chen Hua

Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002

Received:2012-03-26 Revised:2012-05-16 Published:2012-05-09
Supported by:
Project supported by the National Natural Science Foundation of China (Nos.20972039, 21172051), the Medicinal Joint Funds of the Natural Science Foundation of Hebei Province and the Shijiazhuang Pharmaceuitical Group (CSPC) Foundation (Nos.B2011201169, B2012201113), and the Natural Science Foundations of Education Department of Hebei Province (Nos.ZH2011110, Y20111119)

Protected five and six membered azasugar intermediates containing aldehyde group or azide group were synthe-sized using D-mannose as starting material via benzyl amine disubstitution or aza-Wittig reaction, then the oxidation and S_N2 substitution reactions, respectively. The studies on the reaction conditions, the protecting groups and the reaction mechanism were also carried out, providing a protocol to remove trityl (Tr) group selectively.

Key words: azasugar, benzylamine disubstitution, aza-Wittig reaction, trityl, selective deprotection

Cite this article

Li Xiaoliu, Wei Sinan, Zhang Hongbo, Zhang Pingzhu, Wang Wei, Chen Hua. Syntheses of Azasugar Intermediates Containing Aldehyde Group or Azide Group[J]. Chin. J. Org. Chem., 2012, 32(9): 1708-1714.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Horne, G.; Wilson, F. X.; Tinsley, J.; David, H. W.; Richard, S. J. Drug Discovery Today 2011, 16, 107.

[2] Compain, P.; Martin, O. R. Iminosugars: From Synthesis to Therapeutic Applications, John Wiley & Sons Ltd, England, 2007.

[3] Stütz; Arnold, E. Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond, Wiley-VCH, Weinheim, 1999.

[4] Winchester, B. G. Tetrahedron: Asymmetry 2009, 20, 645.

[5] Wrodnigg, T. M.; Steiner, A. J.; Ueberbacher, B. J. Anti-Cancer Agents Med. Chem. 2008, 8, 77.

[6] Natoria, Y.; Imahoria, T.; Murakamia, K.; Yoshimuraa, Y.; Nakagawab, S.; Katob, A.; Adachib, I.; Takahata, H. Bioorg. Med. Chem. Lett. 2011, 21, 738.

[7] Diot, J. D.; Moreno, I. G.; Twigg, G.; Mellet, C. O.; Haupt, K.; Butters, T. D.; Kovensky, J.; Gouin, S. G. J. Org. Chem., 2011, 76, 7757.

[8] Clinch, K.; Evans, G. B.; Frohlich, R. F. G.; Furneaux, R. H.; Kelly, P. M.; Legentil, L.; Murkin, A. S.; Li, L. Schramm, V. L.; Tyler, P. C.; Woolhouse, A. D. J. Med. Chem. 2009, 52, 1126.

[9] de Melo, E. B.; da Silveira, G. A.; Carvalho, I. Tetrahedron 2006, 62, 10277.

[10] Wrodnigg, T. M.; Diness, F.; Gruber, C.; Hä usler, H.; Lundt, I.; Rupitz, K.; Steiner, A. J.; Stütz, A. E.; Tarling, C. A.; Withers, S. G.; Wölfler, H. Bioorg. Med. Chem. 2004, 12, 3485.

[11] Ikeda, K.; Takahashi, M.; Nishida, M.; Miyauchi, M.; Kizu, H.; Kameda, Y.; Arisawa, M.; Watson, A. A.; Nash, R. J.; Fleet, G. W. J.; Asano, N. Carbohydr. Res. 2000, 323, 73.

[12] Afarinkia, K.; Bahar, A. Tetrahedron: Asymmetry 2005, 16, 1239.

[13] Chen, H.; Yin, Q. M.; Li, C. X.; Wang, E. K.; Gao, F.; Zhang, X. B.; Yin, Z.; Wei, S. N.; Li, X. L.; Meng, M.; Zhang, P. Z.; Li, N.; Zhang, J. C. ACS Med. Chem. Lett. 2011, 2, 845.

[14] Li, X. L.; Yin, Q. M.; Jiao, L. L.; Qin, Z. B.; Feng, J. N.; Chen, H.; Zhang, J. C.; Meng, M. Carbohydr. Res. 2011, 346, 401.

[15] Ye, X. S.; Sun, F.; Liu, M.; Li, Q.; Wang, Y. H.; Zhang, G. S.; Zhang, L. H.; Zhang, X. L. J. Med. Chem. 2005, 48, 3688.

[16] Li, X. L.; Zhang, P. Z.; Tian, J.; Duan, K. F.; Chen, H. Chin. J. Org. Chem. 2007, 27, 1013 (in Chinese).(李小六, 张平竹, 田军, 段科芳, 陈华, 有机化学, 2007, 27, 1013.)

[17] Li, X. L.; Qin, Z. B.; Wang, R.; Chen, H.; Zhang, P. Z. Tetrahedron 2011, 67, 1792.

[18] Fleet, G. W. J.; Sona, J. C.; Greenb, D. S. C.; Bellob, I. C.; Winchesterb, B. Tetrahedron 1988, 44, 2649.

[19] Chang, Y. C.; Chir, J. L.; Tsai, S. Y.; Juang, W. F.; Wu, A. T. Tetrahedron Lett. 2009, 50, 4925.

[20] Ménand, M.; Blais, J. C. Valéry, J. M.; Xie, J. J. Org. Chem., 2006, 71, 3295.

[21] Moon, H. R.; Choi, W. J.; Kim, H. O.; Jeong. L. S. Tetrahedron: Asymmetry 2002, 13, 1189.

[22] Davis, B. G. Tetrahedron: Asymmetry 2009, 20, 652.

[23] Curran, T. P.; Pollastri, M. P.; Abelleira, S. M.; Messier, R. J.; Mccollum, T. A.; Rowe, C. G. Tetrahedron Lett. 1994, 35, 5409.

[24] Fleet, G. W. J.; Smith, P. W. Tetrahedron 1987, 47, 979.

含醛基及叠氮基氮杂糖中间体的合成

Syntheses of Azasugar Intermediates Containing Aldehyde Group or Azide Group

PDF

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Jinni Liu, Yibi Xie, Qingqing Yang, Nianyu Huang, Long Wang. Ugi Four-Component Reaction Based on the in situ Capture of Amines and Subsequent Modification Tandem Cyclization Reaction: "One-Pot" Synthesis of Six- and Seven-Membered Heterocycles [J]. Chinese Journal of Organic Chemistry, 2021, 41(6): 2374-2383.
[2]	Hongyan Shi, Ying Zhong, Zhigang Zhao. Synthesis of Multi-substituted 1,4-Dihydroquinoline Derivatives from Morita-Baylis-Hillman (MBH) Carbonates [J]. Chinese Journal of Organic Chemistry, 2021, 41(2): 677-687.
[3]	Zhang Pingzhu, Wei Xiao, Liu Huan, Wang Qiwei, Ma Chen, Rong Ruixue, Li Xiaoliu. Synthesis and Cytotoxicity of Azasugar Modified Anthraquinone Derivatives [J]. Chin. J. Org. Chem., 2016, 36(8): 1921-1925.
[4]	Wu Jing, Kong Hanhan, Ding Mingwu. Synthesis of 12H,14H-Quinazolino[3,4-a]-3,1-benzoxazines [J]. Chin. J. Org. Chem., 2016, 36(7): 1662-1667.
[5]	Wang Hongmei, Guo Shubing, Hu Yanggen, Zeng Xiaohua, Yang Guangyi. Synthesis and Antitumor Activity of Some Novel 5,6,7,8-Tetrahydro- benzo-thieno[2,3-d]pyrimidin-4(3H)-one Derivatives [J]. Chin. J. Org. Chem., 2015, 35(5): 1075-1080.
[6]	Yang Xuhong, Wang Xiang, Wu Minghu. Synthesis and Biological Properties of 3-(2-Hydroxyethyl)-2-(phenylamino)quinazolin-4(3H)-ones [J]. Chin. J. Org. Chem., 2014, 34(5): 1015-1020.
[7]	Liu Jianchao, Liang Ying, He Hongwu. Synthesis and Herbicidal Activity of Thiazolin-2-thione Derivatives [J]. Chin. J. Org. Chem., 2013, 33(9): 1945-1949.
[8]	Chen Li, Sun Shaofa, Song Gongwu. Sequential One-Pot Synthesis of 5,6,8-Trihydropyrano[3',4':4,5]thieno[2,3-d]pyrimidin-4(3H)-one [J]. Chin. J. Org. Chem., 2012, 32(07): 1314-1318.
[9]	FANG Zheng-Dong, LV Jian-Quan. Synthesis of Bridged Bis(thieno[2,3-d]pyrimidin-4(3H)-ones) [J]. Chin. J. Org. Chem., 2011, 31(12): 2102-2105.
[10]	LIU Jian-Chao, HE Hong-Wu, CHEN He-Lian. Synthesis and Fungicidal Activities of 2-(Amino/acetoxy)-3- (4-methylphenyl)-thieno[3,2:5,6]pyrido[4,3-d]- pyrimidin-4(3H)-one Derivatives [J]. Chin. J. Org. Chem., 2011, 31(08): 1208-1212.
[11]	XIAO Lin-Xia, DAN De-Qing. A Convenient Synthesis of 3-[Substituted pyridyl (or thiazolyl)methyl]- 1,2,3-triazolo[4,5-d]pyrimidin-7-one via the Tandem Aza-Wittig Reaction and Their Herbicidal Activity [J]. Chin. J. Org. Chem., 2010, 30(01): 85-91.
[12]	HU Yang-Gen, XU Jing, CHEN Xiao-Bao, JUE Yong-Nian. Synthesis and Fungicidal Activity of 2-Alkoxy(aryloxy)-benzofuro- [3,2-d]pyrimidin-4(3H)-one Derivatives [J]. Chin. J. Org. Chem., 2009, 29(11): 1853-1857.
[13]	LIAO Quan-Bin, LIU Meng-Guo, YU Lan, SHU Min, DING Meng-Wu. Synthesis and Bacteriostatic Activities of 2-Aryloxy-3-(4-fluorophenyl)- 3,5,6,7-tetrahydro-4H-cyclopenta[4,5]thieno[2,3-d]-pyrimidin-4-ones [J]. Chin. J. Org. Chem., 2009, 29(10): 1582-1586.
[14]	LIU Jian-Chao^,a,b,HE Hong-Wu^,a,DING Ming-Wu^a. Synthesis and Biological Activities of 2-(Amino/aroxy)-5,8,9-trimethylthieno[3',2'∶5,6]pyrido[4,3-d]pyrimidin-4(3H)-one Derivatives [J]. Chin. J. Org. Chem., 2008, 28(04): 632-637.
[15]	FU Bo-Qiao,YUAN Ju-Zhen,DING Ming-Wu*. Synthesis and Fungicidal Activities of 4,5-Dihydroimidazo[1,2-b]- 1',2',4'-triazol-4-ones [J]. Chin. J. Org. Chem., 2007, 27(10): 1268-1272.