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Chinese Journal of Organic Chemistry >

2025 , Vol. 45 >Issue 3: 945 - 950

DOI: https://doi.org/10.6023/cjoc202409041

ARTICLES

Synthesis of the Reducing End Fuc-Agl Fragment of Saccharomicins

  • Dengxian Fu ,
  • Shiwei Xu ,
  • Lingkui Meng ,
  • Qian Wan ,
  • Jing Zeng
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  • a Hubei Key Laboratory of Natural Medicinal Chemistry and Resource Evaluation, School of Pharmacy, Tongji Medical College, Huazhong University of Science and Technology, Wuhan 430030
    b School of Pharmaceutical Sciences, Wuhan University, Wuhan 430071
* E-mail: ;
;

Received date: 2024-09-28

  Revised date: 2024-11-14

  Online published: 2024-12-20

Supported by

National Natural Science Foundation of China(22277033); National Natural Science Foundation of China(22077039); National Natural Science Foundation of China(22025102); National Natural Science Foundation of China(22177034)

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Abstract

The Fuc-Agl fragment situated at the reducing terminus of saccharomicins A and B was effectively synthesized. The synthesis encompassed pivotal procedures including taurine assembly, β-glycosidic bond establishment, sulfate ester incorporation, and ultimate deprotection, all of which were executed proficiently, culminating in an aggregate yield of 42.4% across 8 sequential steps.

Key words： saccharomicins; Fuc-Agl fragment; chemical synthesis; sulfation

Cite this article

Dengxian Fu , Shiwei Xu , Lingkui Meng , Qian Wan , Jing Zeng . Synthesis of the Reducing End Fuc-Agl Fragment of Saccharomicins[J]. Chinese Journal of Organic Chemistry, 2025 , 45(3) : 945 -950 . DOI: 10.6023/cjoc202409041

References

[1]
Kong, F.; Zhao, N.; Siegel, M. M.; Janota, K.; Ashcroft, J. S.; Koehn, F. E.; Borders, D. B.; Carter, G. T. J. Am. Chem. Soc. 1998, 120, 13301.
[2]
Singh, M. P.; Petersen, P. J.; Weiss, W. J.; Kong, F.; Greenstein, M. Antimicrob. Agents Chemother. 2000, 44, 2154.
[3]
Pletcher, J. M.; McDonald, F. E. Org. Lett. 2005, 7, 4749.
[4]
Balthaser, B. R.; McDonald, F. E. Org. Lett. 2009, 11, 4850.
[5]
Soliman, S. E.; Bennett, C. S. Org. Lett. 2018, 11, 3413.
[6]
Bylsma, M. B.; Bennett, C. S. Org. Lett. 2018, 20, 4695.
[7]
Jana, M.; Bennett, C. S. Org. Lett. 2018, 20, 7598.
[8]
Carreffi, B. P.; Maney, A. P.; Bennett, C. S. Org. Lett. 2023, 25, 369.
[9]
Carreffi, B. P.; Maney, A. P.; Bennett, C. S. Tetrahedron Lett. 2023, 125, 154615.
[10]
Barpuzary, B.; Kim, M.; Rhee, Y. H. Org. Lett. 2021, 23, 5969.
[11]
Zeng, J.; Wang, R.; Zhang, S.; Fang, J.; Liu, S.; Sun, G.; Xu, B.; Xiao, Y.; Fu, D.; Zhang, W.; Hu, Y.; Wan, Q. J. Am. Chem. Soc. 2019, 141, 8509.
[12]
Zeng, J.; Sun, G.; Yao, W.; Zhu, Y.; Wang, R.; Cai, L.; Liu, K.; Zhang, Q.; Liu, X.-W.; Wan, Q. Angew. Chem., Int. Ed. 2017, 56, 5227.
[13]
Strobel, T.; Al-Dilaimi, A.; Blom, J.; Gessner, A.; Kalinowski, J.; Luzhetska, M.; Pühler, A.; Szczepanowski, R.; Bechthold, A.; Rückert, C. BMC Genomics 2012, 13, 465.
[14]
Zhao, J.; Mo, T.; Li, X.; Ding, W.; Zhang, Q. J. Org. Chem. 2021, 86, 11117.
[15]
Schmidt, R. R.; Michel, J. Angew. Chem., Int. Ed. 1980, 19, 731.
[16]
Fang, J.; Zhu, Y.; Chen, W.; Liu, Y.; Sun, J.; Zeng, J.; Wan, Q. Highlights of Sciencepaper Online 2016, 9, 2030. (in Chinese)
[16]
(方静, 朱阳斌, 陈薇, 刘艳, 孙久长, 曾静, 万谦, 中国科技论文在线精品论文, 2016, 9, 2030.)
[17]
Musicki, B.; Widlanski, T. S. J. Org. Chem. 1990, 55, 4233.
[18]
Xie, M.; Widlanski, T. S. Tetrahedron Lett. 1996, 37, 4443.
[19]
Roberts, J. C.; Gao, H.; Gopalsamy, A.; Kongsjahju, A.; Patch, R. J. Tetrahedron Lett. 1997, 38, 355.
[20]
Pauff, S. M.; Miller, S. C. J. Org. Chem. 2013, 78, 711.
[21]
Marchand-Brynaert, J.; Bouchet, M.; Touillaux, R.; Beauve, C.; Fastrez, J. Tetrahedron 1996, 52, 5591.
[22]
Mancini, R. S.; Lee, J. B.; Taylor, M. S. J. Org. Chem. 2017, 82, 8777.
[23]
Fang, J.; Zeng, J.; Sun, J.; Zhang, S.; Xiao, X.; Lu, Z.; Meng, L.; Wan, Q. Org. Lett. 2019, 21, 6213.
[24]
(a) Nishi, Y.; Yamane, N.; Tanimoto, T. Carbohydr. Res. 2007, 342, 2173.
[24]
(b) Schmidt, R. R.; Wegmann, B.; Jung, K. H. Liebigs Ann. Chem. 1991, 121.
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