Stereoselective Electro-2-deoxyglycosylation from Glycals
Miao Liu
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
These authors contributed equally to this work.
Search for more papers by this authorKai-Meng Liu
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Dr. De-Cai Xiong
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 27 Shanda Nanlu, Jinan, Shandong, 250100 China
Search for more papers by this authorHanyu Zhang
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Search for more papers by this authorTian Li
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Search for more papers by this authorBohan Li
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Search for more papers by this authorXianjin Qin
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Search for more papers by this authorJinhe Bai
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Search for more papers by this authorCorresponding Author
Prof. Xin-Shan Ye
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Search for more papers by this authorMiao Liu
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
These authors contributed equally to this work.
Search for more papers by this authorKai-Meng Liu
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
These authors contributed equally to this work.
Search for more papers by this authorCorresponding Author
Dr. De-Cai Xiong
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, 27 Shanda Nanlu, Jinan, Shandong, 250100 China
Search for more papers by this authorHanyu Zhang
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Search for more papers by this authorTian Li
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Search for more papers by this authorBohan Li
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Search for more papers by this authorXianjin Qin
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Search for more papers by this authorJinhe Bai
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Search for more papers by this authorCorresponding Author
Prof. Xin-Shan Ye
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road No. 38, Beijing, 100191 China
Search for more papers by this authorDedicated to Professor Henry N. C. Wong on the occasion of his 70th birthday
Abstract
We report a novel and highly stereoselective electro-2-deoxyglycosylation from glycals. This method features excellent stereoselectivity, scope, and functional-group tolerance. This process can also be applied to the modification of a wide range of natural products and drugs. Furthermore, a scalable synthesis of glycosylated podophyllotoxin and a one-pot trisaccharide synthesis through iterative electroglycosylations were achieved.
Supporting Information
As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors.
Filename | Description |
---|---|
ange202006115-sup-0001-misc_information.pdf8.9 MB | Supplementary |
Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.
References
- 1
- 1aL. Krasnova, C.-H. Wong, J. Am. Chem. Soc. 2019, 141, 3735–3754;
- 1bC. S. Bennett, Selective Glycosylations: Synthetic Methods and Catalysts: Synthetic Methods and Catalysts, Wiley-VCH, Weinheim, 2017;
10.1002/9783527696239 Google Scholar
- 1cS. C. Hung, M. M. L. Zulueta, Glycochemical Synthesis: Strategies and Applications, First ed., Wiley, Hoboken, 2016;
10.1002/9781119006435 Google Scholar
- 1dA. V. Demchenko, Handbook of Chemical Glycosylation: Advances in Stereoselectivity and Therapeutic Relevance, Wiley-VCH, Weinheim, 2008;
10.1002/9783527621644 Google Scholar
- 1eX. Zhu, R. R. Schmidt, Angew. Chem. Int. Ed. 2009, 48, 1900–1934; Angew. Chem. 2009, 121, 1932–1967.
- 2
- 2aB. La Ferla, C. Airoldi, C. Zona, A. Orsato, F. Cardona, S. Merlo, E. Sironi, G. D'Orazio, F. Nicotra, Nat. Prod. Rep. 2011, 28, 630–648;
- 2bE. K. McCranie, B. O. Bachmann, Nat. Prod. Rep. 2014, 31, 1026–1042.
- 3
- 3aR. W. Gantt, P. Peltier-Pain, J. S. Thorson, Nat. Prod. Rep. 2011, 28, 1811–1853;
- 3bR. D. Goff, J. S. Thorson, MedChemComm 2014, 5, 1036–1047;
- 3cL. Daley, Y. Guminski, P. Demerseman, A. Kruczynski, C. Etiévant, T. Imbert, B. T. Hill, C. Monneret, J. Med. Chem. 1998, 41, 4475–4485;
- 3dQ.-L. He, I. Minn, Q. Wang, P. Xu, S. A. Head, E. Datan, B. Yu, M. G. Pomper, J. O. Liu, Angew. Chem. Int. Ed. 2016, 55, 12035–12039; Angew. Chem. 2016, 128, 12214–12218.
- 4
- 4aS. I. Elshahawi, K. A. Shaaban, M. K. Kharel, J. S. A. Thorson, Chem. Soc. Rev. 2015, 44, 7591–7697;
- 4bR. M. de Lederkremer, C. Marino, Adv. Carbohydr. Chem. Biochem. 2007, 61, 143–216.
- 5For reviews, see:
- 5aC. S. Bennett, M. C. Galan, Chem. Rev. 2018, 118, 7931–7985;
- 5bJ. Zeng, Y. Xu, H. Wang, L. Meng, Q. Wan, Sci. China Chem. 2017, 60, 1162–1179;
- 5cS. Medina, M. C. Galan, Carbohydr. Chem. 2015, 41, 59–89;
10.1039/9781782620600-00059 Google Scholar
- 5dA. Borovika, P. Nagorny, J. Carbohydr. Chem. 2012, 31, 255–283;
- 5eD. Hou, T. L. Lowary, Carbohydr. Res. 2009, 344, 1911–1940;
- 5fC. H. Marzabadi, R. W. Franck, Tetrahedron 2000, 56, 8385–8417;
- 5gJ. Thiem, W. Klaffke, Top. Curr. Chem. 1990, 154, 285–333.
- 6Selected examples of direct synthesis:
- 6aJ. M. Nogueira, M. Bylsma, D. K. Bright, C. S. Bennett, Angew. Chem. Int. Ed. 2016, 55, 10088–10092; Angew. Chem. 2016, 128, 10242–10246;
- 6bK. A. D'Angelo, M. S. Taylor, J. Am. Chem. Soc. 2016, 138, 11058–11066;
- 6cH. Tanaka, A. Yoshizawa, T. Takahashi, Angew. Chem. Int. Ed. 2007, 46, 2505–2507; Angew. Chem. 2007, 119, 2557–2559;
- 6dJ. Zeng, R. Wang, S. Zhang, J. Fang, S. Liu, G. Sun, B. Xu, Y. Xu, D. Fu, W. Zhang, Y. Hu, Q. Wan, J. Am. Chem. Soc. 2019, 141, 8509–8515.
- 7Selected examples of indirect synthesis:
- 7aW. R. Roush, C. E. Bennett, J. Am. Chem. Soc. 1999, 121, 3541–3542;
- 7bK. Toshima, S. Mukaiyama, Y. Nozaki, H. Inokuchi, M. Nakata, K. Tatsuta, J. Am. Chem. Soc. 1994, 116, 9042–9051;
- 7cD. Kahne, D. Yang, J. J. Lim, R. Miller, E. Paguaga, J. Am. Chem. Soc. 1988, 110, 8716–8717;
- 7dD. Hou, H. A. Taha, T. L. Lowary, J. Am. Chem. Soc. 2009, 131, 12937–12948;
- 7eX. Yang, B. Fu, B. Yu, J. Am. Chem. Soc. 2011, 133, 12433–12435.
- 8Selected example of de novo synthesis: R. S. Babu, Q. Chen, S. W. Kang, M. Zhou, G. A. O'Doherty, J. Am. Chem. Soc. 2012, 134, 11952–11955.
- 9For selected examples of anomeric O-alkylation, see:
- 9aJ. P. Issa, C. S. Bennett, J. Am. Chem. Soc. 2014, 136, 5740–5744;
- 9bD. Zhu, K. N. Baryal, S. Adhikari, J. Zhu, J. Am. Chem. Soc. 2014, 136, 3172–3175.
- 10Examples of anomeric C-alkyloxylation: K. M. Hoang, N. R. Lees, S. B. Herzon, J. Am. Chem. Soc. 2019, 141, 8098–8103.
- 11
- 11aB. D. Sherry, R. N. Loy, F. D. Toste, J. Am. Chem. Soc. 2004, 126, 4510–4511;
- 11bA. Sau, R. Williams, C. Palo-Nieto, A. Franconetti, S. Medina, M. C. Galan, Angew. Chem. Int. Ed. 2017, 56, 3640–3644; Angew. Chem. 2017, 129, 3694–3698;
- 11cC. Palo-Nieto, A. Sau, M. C. Galan, J. Am. Chem. Soc. 2017, 139, 14041–14044.
- 12
- 12aE. I. Balmond, D. M. Coe, M. C. Galan, E. M. McGarrigle, Angew. Chem. Int. Ed. 2012, 51, 9152–9155; Angew. Chem. 2012, 124, 9286–9289;
- 12bE. I. Balmond, D. Benito-Alifonso, D. M. Coe, R. W. Alder, E. M. McGarrigle, M. C. Galan, Angew. Chem. Int. Ed. 2014, 53, 8190–8194; Angew. Chem. 2014, 126, 8329–8333;
- 12cS. Das, D. Pekel, J. M. Neudorfl, A. Berkessel, Angew. Chem. Int. Ed. 2015, 54, 12479–12483; Angew. Chem. 2015, 127, 12656–12660;
- 12dR. Williams, M. C. Galan, Eur. J. Org. Chem. 2017, 6247–6264.
- 13G. Zhao, T. Wang, Angew. Chem. Int. Ed. 2018, 57, 6120–6124; Angew. Chem. 2018, 130, 6228–6232.
- 14
- 14aE. J. Horn, B. R. Rosen, P. S. Baran, ACS Cent. Sci. 2016, 2, 302–308;
- 14bR. D. Little, K. D. Moeller, Chem. Rev. 2018, 118, 4483–4484.
- 15Selected reviews:
- 15aM. Yan, Y. Kawamata, P. S. Baran, Chem. Rev. 2017, 117, 13230–13319;
- 15bR. Francke, R. D. Little, Chem. Soc. Rev. 2014, 43, 2492–2521;
- 15cC. Gütz, B. Klöckner, S. R. Waldvogel, Org. Process Res. Dev. 2016, 20, 26–32;
- 15dY. Jiang, K. Xu, C. Zeng, Chem. Rev. 2018, 118, 4485–4540;
- 15eS. Tang, Y. Liu, A. Lei, Chem 2018, 4, 27–45;
- 15fC. Ma, P. Fang, T.-S. Mei, ACS Catal. 2018, 8, 7179–7189;
- 15gA. Wiebe, T. Gieshoff, S. Mçhle, E. Rodrigo, M. Zirbes, S. R. Waldvogel, Angew. Chem. Int. Ed. 2018, 57, 5594–5619; Angew. Chem. 2018, 130, 5694–5721.
- 16R. Noyori, I. Kurimoto, J. Org. Chem. 1986, 51, 4320–4322.
- 17Selected reviews:
- 17aA. Shimizu, R. Hayashi, J. Yoshida, Chem. Rev. 2018, 118, 4702–4730;
- 17bS. Manmode, K. Matsumoto, T. Nokami, T. Itoh, Asian J. Org. Chem. 2018, 7, 1719–1729;
- 17cJ. Yoshida, K. Kataoka, R. Horcajada, A. Nagaki, Chem. Rev. 2008, 108, 2265–2299;
- 17dT. Nokami, Trends Glycosci. Glycotechnol. 2019, 31, SE74–SE75.
- 18Selected examples:
- 18aT. Nokami, A. Shibuya, H. Tsuyama, S. Suga, A. A. Bowers, D. Crich, J. Yoshida, J. Am. Chem. Soc. 2007, 129, 10922–10928;
- 18bT. Nokami, R. Hayashi, Y. Saigusa, A. Shimizu, C.-Y. Liu, K.-K. Tony Mong, J. Yoshida, Org. Lett. 2013, 15, 4520–4523;
- 18cT. Nokami, Y. Nozaki, Y. Saigusa, A. Shibuya, S. Manabe, Y. Ito, J. Yoshida, Org. Lett. 2011, 13, 1544–1547;
- 18dT. Nokami, A. Shibuya, S. Manabe, Y. Ito, J. Yoshida, Chem. Eur. J. 2009, 15, 2252–2255;
- 18eT. Nokami, H. Tsuyama, A. Shibuya, T. Nakatsutsumi, J. Yoshida, Chem. Lett. 2008, 37, 942–943;
- 18fT. Nokami, Y. Isoda, N. Sasaki, A. Takaiso, S. Hayase, T. Itoh, R. Hayashi, A. Shimizu, J. Yoshida, Org. Lett. 2015, 17, 1525–1528;
- 18gS. Yamago, K. Kokubo, O. Hara, S. Masuda, J. Yoshida, J. Org. Chem. 2002, 67, 8584–8592.
- 19
- 19aY. Wu, D.-C. Xiong, S.-C. Chen, Y.-S. Wang, X.-S. Ye, Nat. Commun. 2017, 8, 14851;
- 19bL. Sun, X. Wu, D.-C. Xiong, X.-S. Ye, Angew. Chem. Int. Ed. 2016, 55, 8041–8044; Angew. Chem. 2016, 128, 8173–8176;
- 19cX.-F. Huang, L.-J. Huang, H.-S. Wang, X.-S. Ye, Angew. Chem. Int. Ed. 2004, 43, 5221–5224; Angew. Chem. 2004, 116, 5333–5336.
- 20J. Arai, J. Appl. Electrochem. 2002, 32, 1071–1079.
- 21X. Gu, L. Chen, X. Wang, X. Liu, Q. You, W. Xi, L. Gao, G. Chen, Y.-L. Chen, B. Xiong, J. Shen, J. Org. Chem. 2014, 79, 1100–1110.
- 22S. Bansal, S. Vyas, S. Bhattacharya, M. Sharma, Nat. Prod. Rep. 2013, 30, 1438–1454.
- 23
- 23aB. Bennett, J. Chang, A. J. Bard, Electrochim. Acta 2016, 219, 1–9;
- 23bL. S. Kang, M. H. Luo, C. M. Lam, L. M. Hu, R. D. Little, C. C. Zeng, Green Chem. 2016, 18, 3767–3774;
- 23cI. Damljanović, D. Stevanović, M. Vukicević, R. D. Vukicević, Carbohydr. Res. 2011, 346, 2683–2687.
- 24We thank a reviewer for calling our attention to the presence of trace amounts of bromide and suggestion of control experiments with the addition of an alternative bromide source.
- 25We were able to rule out an acid-catalyzed glycosylation process (entry 12 in Table S6, Table S7, and Ref. [11b]) and a bromoglycosylation/debromination pathway (see Section S7.3 in the Supporting Information) by control experiments.
- 26
- 26aK. D. Moeller, M. R. Marzabadi, D. G. New, M. Y. Chiang, S. Keith, J. Am. Chem. Soc. 1990, 112, 6123–6124;
- 26bA. Sutterer, K. D. Moeller, J. Am. Chem. Soc. 2000, 122, 5636–5637;
- 26cJ. M. Campbell, H.-C. Xu, K. D. Moeller, J. Am. Chem. Soc. 2012, 134, 18338–18344;
- 26dC.-Y. Cai, X.-M. Shu, H.-C. Xu, Nat. Commun. 2019, 10, 4953;
- 26eCVs of glycals: T. Linker, D. Schanzenbach, E. Elamparuthi, T. Sommermann, W. Fudickar, V. Gyóllai, L. Somsák, W. Demuth, M. Schmittel, J. Am. Chem. Soc. 2008, 130, 16003–16010.
- 27S. Sumino, A. Fusano, I. Ryu, Org. Lett. 2013, 15, 2826–2829.
- 28
- 28aA. Nowacki, D. Walczak, B. Liberek, Carbohydr. Res. 2012, 352, 177–185;
- 28bA. Nowacki, D. Walczak, B. Liberek, Carbohydr. Res. 2018, 462, 13–27.
- 29B. Giese, Angew. Chem. Int. Ed. Engl. 1989, 28, 969–980; Angew. Chem. 1989, 101, 993–1004.
Citing Literature
This is the
German version
of Angewandte Chemie.
Note for articles published since 1962:
Do not cite this version alone.
Take me to the International Edition version with citable page numbers, DOI, and citation export.
We apologize for the inconvenience.