光诱导的糖类化合物的合成与修饰
收稿日期: 2018-04-18
修回日期: 2018-05-12
网络出版日期: 2018-05-17
基金资助
湖北省自然科学基金（Nos.2015CFC818，2015CFA033）、黄冈师范学院培育基金（No.201615503）、黄冈师范学院博士基金（No.2015001703）资助项目.
Photo-Induced Carbohydrate Synthesis and Modification
Received date: 2018-04-18
Revised date: 2018-05-12
Online published: 2018-05-17
Supported by
Project supported by Natural Science Foundation of Hubei Province (Nos. 2015CFC818, 2015CFA033), the Cultivation Fund Project of Huanggang Normal University (No. 201615503) and the Doctoral Fund Project of Huanggang Normal University (No. 2015001703).
叶辉 , 肖聪 , 陆良秋 . 光诱导的糖类化合物的合成与修饰[J]. 有机化学, 2018 , 38(8) : 1897 -1906 . DOI: 10.6023/cjoc201804035
The synthesis of carbohydrates through photoredox catalysis has achieved a great process in the past decade. This review highlights the latest advances in this research area, including the photo-induced O-glycosylation and C-glycosylation, and the functional group modification and thiol-ene coupling reactions of carbohydrates.
[1] (a) Kitamura, K.; Ando, Y.; Matsumoto, T.; Suzuki, K. Chem. Rev. 2018, 118, 1495.
(b) Wang, H.-Y.; Blaszczyk, S. A.; Xiao, G.; Tang, W. Chem. Soc. Rev. 2018, 47, 681.
[2] (a) Yang, Y.; Zhang, X.; Yu, B. Nat. Prod. Rep. 2015, 32, 1331.
(b) Yang, Y.; Yu, B. Chem. Rev. 2017, 117, 12281.
(c) Zeng, J.; Xu, Y.; Wang, H.; Meng, L.; Wan, Q. Sci. China Chem. 2017, 60, 1162.
[3] (a) Wu, Y.; Xiong, D.-C.; Chen, S.-C.; Wang, Y.-S.; Ye, X.-S. Nat. Commun. 2017, 8, 14851.
(b) Yu, B. Acc. Chem. Res. 2018, 51, 507.
(c) Gao, P.-P.; Zhu, S.-Y.; Cao, H.; Yang, J.-S. J. Am. Chem. Soc. 2016, 138, 1684.
(d) Qin, C.; Schumann, B.; Zou, X.; Pereira, C. L.; Tian, G.; Hu, J.; Seeberger, P. H.; Yin, J. J. Am. Chem. Soc. 2018, 140, 3120.
(e) Zhou, X.; Wang, P.; Zhang, L.; Chen, P.; Ma, M.; Song, N.; Ren, S.; Li, M. J. Org. Chem. 2018, 83, 588.
(f) Shu, P.; Xiao, X.; Zhao, Y.; Tao, J.; Wang, H.; Lu, Z.; Yao, G.; Zeng, J.; Wan, Q. Angew. Chem., Int. Ed. 2015, 54, 14432.
(g) Xiao, X.; Zhao, Y.; Shu, P.; Zhao, X.; Liu, Y.; Sun, J.; Zhang, Q.; Zeng, J.; Wan, Q. J. Am. Chem. Soc. 2016, 138, 13402.
[4] (a) Prier, C. K.; Rankic, D. A.; MacMillan, D. W. C. Chem. Rev. 2013, 113, 5322.
(b) Schultz, D. M.; Yoon, T. P. Science 2014, 343, 985.
(c) Chen, J.-R.; Hu, X.-Q.; Lu, L.-Q.; Xiao, W.-J. Acc. Chem. Res. 2016, 49, 1911.
(d) Guan, B.; Xu, X.; Wang, H.; Li, X. Chin. J. Org. Chem. 2016, 36, 1564(in Chinese). (关保川, 许孝良, 王红, 李小年, 有机化学, 2016, 36, 1564.)
(e) Ravelli, D.; Protti, S.; Fagnoni, M. Chem. Rev. 2016, 116, 9850.
(f) Kärkäs, M. D.; Porco, Jr., J. A.; Stephenson, C. R. J. Chem. Rev. 2016, 116, 9683.
(g) Liu, Q.; Wu, L.-Z. Natl. Sci. Rev. 2017, 4, 359.
(h) Song, H.; Liu, X.; Qin, Y. Acta Chim. Sinica 2017, 75, 1137(in Chinese). (宋颢, 刘小宇, 秦勇, 化学学报, 2017, 75, 1137.)
(i) Li, W.; Xu, W.; Xie, J.; Yu, S.; Zhu, C. Chem. Soc. Rev. 2018, 47, 654.
[5] Sangwan, R.; Mandal, P. K. RSC Adv. 2017, 7, 26256.
[6] Hashimoto, S.; Kurimoto, I; Fujii, Y.; Noyori, R. J. Am. Chem. Soc. 1985, 107, 1427.
[7] Wen, P.; Crich, D. Org. Lett. 2017, 19, 2402.
[8] Iwata, R.; Uda, K.; Takahashi, D.; Toshima, K. Chem. Commun. 2014, 50, 10695.
[9] Kimura, T.; Eto, T.; Takahashi, D.; Toshima, K. Org. Lett. 2016, 18, 3190.
[10] Griffin, G. W.; Bandara, N. C.; Clarke, M. A.; Tsang, W.-S.; Garegg, P. J.; Oscarson, S.; Silwanis, B. A. Heterocycles 1990, 30, 939.
[11] Nakanishi, M.; Takahashi, D.; Toshima, K. Org. Biomol. Chem. 2013, 11, 5079.
[12] Wever, W. J.; Cinelli, M. A.; Bowers, A. B. Org. Lett. 2013, 15, 30.
[13] Mao, R.-Z.; Guo, F.; Xiong, D.-C.; Li, Q.; Duan, J.; Ye, X.-S. Org. Lett. 2015, 17, 5606.
[14] Mao, R.-Z.; Xiong, D.-C.; Guo, F.; Li, Q.; Duan, J.; Ye, X.-S. Org. Chem. Front. 2016, 3, 737.
[15] Yu, Y.; Xiong, D.-C.; Mao, R.-Z.; Ye, X.-S. J. Org. Chem. 2016, 81, 7134.
[16] Spell, M. L.; Deveaux, K.; Bresnahan, C. G.; Bernard, B. L.; Sheffield, W.; Kumar, R.; Ragains, J. R. Angew. Chem., Int. Ed. 2016, 55, 6515.
[17] Furuta, T.; Takeuchi, K.; Iwamura, M. Chem. Commun. 1996, 157.
[18] Cumpstey, I.; Crich, D. J. Carbohydr. Chem. 2011, 30, 469.
[19] Spell, M.; Wang, X.; Wahba, A. E.; Conner, E.; Ragains, J. Carbohydr. Res. 2013, 369, 42.
[20] Andrews, R. S.; Becker, J. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2010, 49, 7274.
[21] Andrews, R. S.; Becker, J. J.; Gagné, M. R. Angew. Chem., Int. Ed. 2012, 51, 4140.
[22] Andrews, R. S.; Becker, J. J.; Gagné, M. R. Org. Lett. 2011, 13, 2406.
[23] Wang, H.; Tao, J.; Cai, X.; Chen, W.; Zhao, Y.; Xu, Y.; Yao, W.; Zeng, J.; Wan, Q. Chem.-Eur. J. 2014, 20, 17319.
[24] Xue, W.; Yuan, X.; Cheng, S.; Shi, Y. Synthesis 2014, 46, 331.
[25] Dai, C.; Narayanam, J. M.; Stephenson, C. R. Nat. Chem. 2011, 3, 140.
[26] Wang, B.; Xiong, D.-C.; Ye, X.-S. Org. Lett. 2015, 17, 5698.
[27] Rasool, F.; Bhat, A. H.; Hussain, N.; Mukherjee, D. Chemis-trySelect 2016, 1, 6553.
[28] Gao, X.-F.; Du, J.-J.; Liu, Z.; Guo, J. Org. Lett. 2016, 18, 1166.
[29] (a) Wittrock, S.; Becker, T.; Kunz, H. Angew. Chem., Int. Ed. 2007, 46, 5226.
(b) Dondoni, A. Angew. Chem., Int. Ed. 2008, 47, 8995.
(c) Floyd, N.; Vijayakrishnan, B.; Koeppe, J. R.; Davis, B. G. Angew. Chem., Int. Ed. 2009, 48, 7798.
(d) Kramer, J. R.; Deming, T. J. J. Am. Chem. Soc. 2010, 132, 15068.
(e) Tucker-Schwartz, A. K.; Farrell, R. A.; Garrell, R. L. J. Am. Chem. Soc. 2011, 133, 11026.
(f) Wojcik, F.; O'Brien, A. G.; Goetze, S.; Seeberger, P. H. Chem. Eur. J. 2013, 19, 3090.
[30] Limnios, D.; Kokotos, C. G. Adv. Synth. Catal. 2017, 359, 323.
[31] Zhao, G.; Kaur, S.; Wang, T. Org. Lett. 2017, 19, 3291.
/
| 〈 |
|
〉 |
