Strategies toward protecting group-free glycosylation through selective activation of the anomeric center

A. Michael Downey and Michal Hocek
Beilstein J. Org. Chem. 2017, 13, 1239–1279. https://doi.org/10.3762/bjoc.13.123

Cite the Following Article

Strategies toward protecting group-free glycosylation through selective activation of the anomeric center
A. Michael Downey and Michal Hocek
Beilstein J. Org. Chem. 2017, 13, 1239–1279. https://doi.org/10.3762/bjoc.13.123

How to Cite

Downey, A. M.; Hocek, M. Beilstein J. Org. Chem. 2017, 13, 1239–1279. doi:10.3762/bjoc.13.123

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.

Presentation Graphic

Picture with graphical abstract, title and authors for social media postings and presentations.
Format: PNG Size: 129.9 KB Download

Citations to This Article

Up to 20 of the most recent references are displayed here.

Scholarly Works

  • Wang, P.; Cheng, T.; Pan, J. Nucleoside Analogs: A Review of Its Source and Separation Processes. Molecules (Basel, Switzerland) 2023, 28, 7043. doi:10.3390/molecules28207043
  • Li, G.; Noguchi, M.; Ishihara, M.; Takagi, Y.; Nagaki, M.; Saito, S.; Saito, M.; Ye, X.-S.; Shoda, S.-I. Stereoselective protecting-group-free synthesis of alkyl glycosides using dibenzyloxy triazine type glycosyl donors. Carbohydrate research 2023, 534, 108940. doi:10.1016/j.carres.2023.108940
  • Qiu, X.; Chong, D.; Fairbanks, A. J. Selective Anomeric Acetylation of Unprotected Sugars with Acetic Anhydride in Water. Organic letters 2023, 25, 1989–1993. doi:10.1021/acs.orglett.3c00584
  • Kano, K.; Ishii, N.; Miyagawa, A.; Takeda, H.; Hirabayashi, Y.; Kamiguchi, H.; Greimel, P.; Matsuo, I. Protecting-group-free glycosylation of phosphatidic acid in aqueous media. Organic & biomolecular chemistry 2023, 21, 2138–2142. doi:10.1039/d2ob02173k
  • Chen, Q.-Q.; Zhao, Z.-R.; Patehebieke, Y.; Wang, X. Regioselective ribonucleoside synthesis through Ti-catalysed ribosylation of nucleobases. Nature Synthesis 2023, 2, 348–356. doi:10.1038/s44160-022-00206-1
  • Wang, Z.; Maisonneuve, S.; Xie, J. One-Pot Synthesis of Water-Soluble Glycosyl Azobenzenes and Their Photoswitching Properties in Water. The Journal of organic chemistry 2022, 87, 16165–16174. doi:10.1021/acs.joc.2c01511
  • Dhara, D.; Dhara, A.; Murphy, P. V.; Mulard, L. A. Protecting group principles suited to late stage functionalization and global deprotection in oligosaccharide synthesis. Carbohydrate research 2022, 521, 108644. doi:10.1016/j.carres.2022.108644
  • Dey, K.; Jayaraman, N. Pyridoneimine-catalyzed anomeric aqueous oxa-Michael additions of native mono- and disaccharides. Carbohydrate research 2022, 520, 108610. doi:10.1016/j.carres.2022.108610
  • Hamaya, Y.; Komura, N.; Imamura, A.; Ishida, H.; Ando, H.; Tanaka, H.-N. Protecting-group- and microwave-free synthesis of β-glycosyl esters and aryl β-glycosides of N-acetyl-d-glucosamine. Bioorganic & medicinal chemistry 2022, 67, 116852. doi:10.1016/j.bmc.2022.116852
  • Qiu, X.; Garden, A. L.; Fairbanks, A. J. Protecting group free glycosylation: one-pot stereocontrolled access to 1,2-trans glycosides and (1→6)-linked disaccharides of 2-acetamido sugars. Chemical science 2022, 13, 4122–4130. doi:10.1039/d2sc00222a
  • Shi, H.; Yang, J.; Cheng, Y.; Yang, J.; Lu, X.; Ma, X. 1, 2-trans-Stereoselective 7-O-Glycosylation of Flavonoids with Unprotected Pyranoses by Mitsunobu Reaction. Chemistry, an Asian journal 2022, 17, e202200120. doi:10.1002/asia.202200120
  • Dey, K.; Jayaraman, N. Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions. Chemical communications (Cambridge, England) 2022, 58, 2224–2227. doi:10.1039/d1cc07056h
  • Vera, C.; Guerrero, C.; Illanes, A. Trends in lactose-derived bioactives: synthesis and purification. Systems Microbiology and Biomanufacturing 2022, 2, 393–412. doi:10.1007/s43393-021-00068-2
  • Wen, P.; Jia, P.; Fan, Q.; McCarty, B. J.; Tang, W. Streamlined Iterative Assembly of Thio-Oligosaccharides by Aqueous S-Glycosylation of Diverse Deoxythio Sugars. ChemSusChem 2022, 15, e202102483. doi:10.1002/cssc.202102483
  • Ueda, Y. Site-Selective Molecular Transformation: Acylation of Hydroxy Groups and C-H Amination. Chemical & pharmaceutical bulletin 2021, 69, 931–944. doi:10.1248/cpb.c21-00425
  • Rajendran, D.; Bhagavathsingh, J. O-Galactosylation of Diphenolic Compounds Using Boc Activation: A Convenient Chemical Synthesis. ChemistrySelect 2021, 6, 8919–8922. doi:10.1002/slct.202102564
  • Basu, N.; Ghosh, R. Recent chemical syntheses of bacteria related oligosaccharides using modern expeditious approaches. Carbohydrate research 2021, 507, 108295. doi:10.1016/j.carres.2021.108295
  • Candito, D. A.; Ye, Y.; Quiroz, R. V.; Reutershan, M. H.; Witter, D. J.; Gadamsetty, S. B.; Li, H.; Saurí, J.; Schneider, S.; Lam, Y.-h.; Palte, R. L. Development of a Flexible and Robust Synthesis of Tetrahydrofuro[3,4-b]furan Nucleoside Analogues. The Journal of organic chemistry 2021, 86, 5142–5151. doi:10.1021/acs.joc.0c02969
  • Zhang, G.-L.; Gadi, M. R.; Cui, X.; Liu, D.; Zhang, J.; Saikam, V.; Gibbons, C.; Wang, P. G.; Li, L. Protecting-group-free S-glycosylation towards thioglycosides and thioglycopeptides in water. Green chemistry : an international journal and green chemistry resource : GC 2021, 23, 2907–2912. doi:10.1039/d1gc00098e
  • Walther, R.; Zelikin, A. N. Chemical (neo)glycosylation of biological drugs. Advanced drug delivery reviews 2021, 171, 62–76. doi:10.1016/j.addr.2021.01.021
Other Beilstein-Institut Open Science Activities