ARTICLE

Efficient Synthesis of Epilactose

  • Wang Jiayao ,
  • Jiang Rui ,
  • Liang Xiaomei ,
  • Jin Shuhui ,
  • Wang Daoquan ,
  • Zhang Jianjun
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  • China Agricultural University, Beijing 100193

Received date: 2016-08-17

  Revised date: 2016-10-08

  Online published: 2016-11-03

Supported by

Project supported by the National Science & Technology Pillar Program of China (No. 2015BAK45B01).

Abstract

Epilactose (4-O-β-D-galactopyranosyl-D-mannose) is a reducing disaccharide with satisfactory prebiotic properties. A superior synthetic methods were confirmed by screening different coupled donors and acceptors which were synthesized from D-mannose and D-galactose, respectively. This route gets 50% overall yields and all the intermediates are easily to be purified, making the route suitable for large scale preparation of the target compound. All the compounds were characterized by NMR and HRMS spectra.

Cite this article

Wang Jiayao , Jiang Rui , Liang Xiaomei , Jin Shuhui , Wang Daoquan , Zhang Jianjun . Efficient Synthesis of Epilactose[J]. Chinese Journal of Organic Chemistry, 2017 , 37(2) : 375 -384 . DOI: 10.6023/cjoc201608010

References

[1] Olano, A.; Calvo, M. M. Food Chem. 1989, 34, 239.
[2] Watanabe, J.; Nishimukai, M.; Taguchi, H.; Senoura, T.; Hamada, S.; Matsui, H.; Yamamoto, T.; Wasaki, J.; Hara, H.; Ito, S. J. Dairy Sci. 2008, 91, 4518.
[3] Nishimukai, M.; Watanabe, J.; Taguchi, H.; Senoura, T.; Hamada, S.; Matsui, H.; Yamamoto, T.; Wasaki, J.; Hara, H.; Ito, S. J Agric. Food Chem. 2008, 56, 10340.
[4] Suzuki, T.; Nishimukai, M.; Shinoki, A.; Taguchi, H.; Fukiya, S.; Yokota, A.; Saburi, W.; Yamamoto, T.; Hara, H.; Matsui, H. J. Agric. Food Chem. 2010, 58, 10787.
[5] Murakami, Y.; Ojima-Kato, T.; Saburi, W.; Mori, H.; Matsui, H.; Tanabe, S.; Suzuki, T. Br. J. Nutr. 2015, 114(11), 1774.
[6] Bergmann, M.; Justus, L. Ann. Chem. 1923, 434, 79.
[7] Haskins, W. T.; Hann, R. M.; Hudson, C. S. J. Am. Chem. Soc. 1942, 64, 1852.
[8] Huang, S.; Yu, H.; Chen, X. Angew. Chem., Int. Ed. 2007, 46, 2249.
[9] Ito, S.; Taguchi, H.; Hamada, S.; Kawauchi, S.; Ito, H.; Senoura, T.; Watanabe, J.; Nishimukai, M.; Matsui, H. Appl. Microbiol. Biotechnol. 2008, 79, 433.
[10] Tyler, T. R.; Leatherwood, J. M. Arch. Biochem. Biophys. 1967, 119, 363.
[11] Zong, G. H.; Liang, X. M.; Zhang, J. J.; Duan, L. S.; Tan, W. M.; Wang, D. Q. Carbohydr. Res. 2014, 388, 87.
[12] Jiang, R.; Liang, X. M.; Jin, S. H.; Zhang, J. J.; Wang, D. Q. Chin. J. Org. Chem. 2014, 34, 926 (in Chinese).(姜锐, 梁晓梅, 金淑慧, 张建军, 王道全, 有机化学, 2014, 34, 926.)
[13] Jiang, R.; Zong, G. H.; Liang, X. M.; Jin, S. H.; Dong, Y. H.; Wang, D. Q.; Zhang, J. J. Synthesis 2015, 47, A~J.
[14] Jiang, R.; Zong, G. H.; Liang, X. M.; Jin, S. H.; Zhang, J. J.; Wang, D. Q. Molecules 2014, 19, 6683.
[15] Zong, G. H.; Yu, N. L.; Xu, Y. J.; Zhang, J. J.; Wang, D. Q.; Liang, X. M. Synthesis 2010, 10, 1666.
[16] Chung, S.-K.; Moon, S.-H. Carbohydr. Res. 1994, 260, 39.
[17] Richard, R.; Schmidt; Josef, Michell. Angew. Chem., Int. Ed. Engl. 1980, 19, 731.
[18] Blattner; Regine. Carbohydr. Res. 2006, 341(3), 299.
[19] Rio, S.; Beau, J. M.; Jacquinet, J. C. Carbohydr. Res. 1991, 219, 71.
[20] Mariko, M.; Katsumi, A. Biosci. Biotechnol. Biochem. 2004, 68(10), 2086.
[21] Yde, M.; De Bruyne, C. K. Carbohydr. Res. 1973, 26(1), 227.
[22] Mao, R. Z.; Guo, F.; Xiong, D. C.; Li, Q.; Duan, J.Y.; Ye, X.S. Org. Lett. 2015, 17(22), 5606.
[23] Corcilius, L.; Payne, R. J. Org. Lett. 2013, 15(22), 5794.

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