Synthesis of 2,2-Bis-C-functionalized Chain Glucosid-3-ketals
Corresponding Author
Fuyi Zhang
Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan 450052, China
Fuyi Zhang, Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan 450052, China, Tel.: +86-371-67763845; Fax: +86-371-67763845
Hongmin Liu, School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, Henan 450001, China
Search for more papers by this authorHong Liu
Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan 450052, China
Search for more papers by this authorYingming Sheng
Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan 450052, China
Search for more papers by this authorCorresponding Author
Hongmin Liu
School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, Henan 450001, China
Fuyi Zhang, Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan 450052, China, Tel.: +86-371-67763845; Fax: +86-371-67763845
Hongmin Liu, School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, Henan 450001, China
Search for more papers by this authorCorresponding Author
Fuyi Zhang
Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan 450052, China
Fuyi Zhang, Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan 450052, China, Tel.: +86-371-67763845; Fax: +86-371-67763845
Hongmin Liu, School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, Henan 450001, China
Search for more papers by this authorHong Liu
Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan 450052, China
Search for more papers by this authorYingming Sheng
Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan 450052, China
Search for more papers by this authorCorresponding Author
Hongmin Liu
School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, Henan 450001, China
Fuyi Zhang, Chemistry Department, The Key Lab of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou, Henan 450052, China, Tel.: +86-371-67763845; Fax: +86-371-67763845
Hongmin Liu, School of Pharmaceutical Sciences, Zhengzhou University, Zhengzhou, Henan 450001, China
Search for more papers by this authorAbstract
Novel 2,2-bis-C-functionalized chain glucosid-3-uloses have been synthesized in the form of ketal. The synthesis is rather convenient through one pot multistep reactions and no expensive reagents are involved. The products are formed via autoxidation-Michael addition mechanism and their structures were characterized by X-ray crystallographic analysis. Their crystal stuctures are stablilized by intermolecular hydrogen bonds and double-strand supramolecular stacking is observed.
REFERENCES
- 1 Das, I.; Pal, T. K.; Suresh, C. G.; Pathak, T.. J. Org. Chem., 2007, 72, 5523.
- 2 Sanki, A. K.; Suresh, C. G.; Falgune, U. D.; Pathak, T.. Org Lett., 2003, 5, 1285.
- 3 Jones, N. A.; Nepogodiev, S. A.; MacDonald, C. J.; Hughes, D. L.; Field, R. A.. J. Org. Chem., 2005, 70, 8556.
- 4 Pathak, T.; Bhattacharya, R.. Carbohydr. Res., 2008, 343, 1980.
- 5 Wang, N.; Li, J.; Czyryca, P. G.; Chang, H.; Kao, J.; Chang, C. K.. Bioorg. Med. Lett., 2004, 14, 4389.
- 6 Liu, H.-M.; Zou, D.-P.; Zhang, F.; Zhu, W.-G.; Peng, T.. Eur. J. Org. Chem., 2004, 10, 2103.
- 7 Liu, H.-M.; Zhang, F.; Zhang, J.. Carbohydr. Res., 2001, 334, 323.
- 8 Wood, A. J.; Holt, D. J.; Dominguez, M. C.; Jenkins, P. R.. J. Org. Chem., 1998, 63, 8522.
- 9 Bonnert, R. V.; Jenkins, P. R.. J. Chem. Soc., Chem. Commun., 1987, 6.
- 10 Bonnert, R. V.; Howarth, J.; Jenkins, P. R.; Lawrence, N. J.. J. Chem. Soc., Perkin. Trans 1, 1991, 1225.
- 11 EI-Naggar, L. J.; Beal, J. L.. J. Nat. Prod., 1980, 43, 649.
- 12 Liu, H.-M.; Tsuda, Y.. Chem. Pharm. Bull., 1996, 44, 80.
- 13 Liu, H.-M.; Xu, W.; Liu, Z.-Z.. Carbohydr. Res., 2001, 331, 229.
- 14 Zhang, F.; Du, C.-X.; Liu, H.-M.; Zhu, Y.. Acta Crystallogr. Sect. C, 2001, 57, 1361.
- 15 Liu, H.-M.; Zhang, F.; Wang, S.. Org. Biomol. Chem., 2003, 1, 1641.
- 16 Liu, H.-M.; Zhang, F.; Xu, W.; Li, S.. Acta Chim. Sinica, 2003, 61, 1149 (in Chinese).
- 17 Liu, H.-M.; Zhang, F.; Zhang, J.; Li, S.. Carbohydr. Res., 2003, 338, 1737.
