Utilizing Reusable Catalyst Phosphotungstic Acid for the Synthesis of Thioglycoside from Per- O-acetyl Saccharides with Microwave-Assisted and De- O-acetylation with Methanol
- PMID: 36910976
- PMCID: PMC9996587
- DOI: 10.1021/acsomega.3c00362
Utilizing Reusable Catalyst Phosphotungstic Acid for the Synthesis of Thioglycoside from Per- O-acetyl Saccharides with Microwave-Assisted and De- O-acetylation with Methanol
Abstract
Traditional methods for synthesizing complex oligosaccharides currently developed are not efficient, requiring a new glycosylation methodology. Herein, using phosphotungstic acid (PTA) as a catalyst has demonstrated to be a simple possibility for carbohydrate synthesis. The methodology is engineered into a PTA-catalyzed thioglycoside preparation under microwave conditions and de-O-acetylation of carbohydrates. These easier operations and convenient protocols display a wide substrate scope. Moreover, both methods can be developed into a one-pot reaction for the efficient synthesis of carbohydrate analogues.
© 2023 The Authors. Published by American Chemical Society.
Conflict of interest statement
The authors declare no competing financial interest.
References
-
- Shie C.-R.; Tzeng Z.-H.; Wang C.-C.; Hung S.-C. Metal Trifluoromethanesulfonate-Catalyzed Regioselective Reductive Ring Opening of Benzylidene Acetals. J. Chin. Chem. Soc. 2009, 56, 510–523. 10.1002/jccs.200900076. - DOI
- Chen J.-S.; Pantawane A. R.; Huang P.-H.; Liu J.-W.; Sankar A.; Lin Y.-J.; Liu Y.-H.; Wu H.-R.; Luo S.-Y. One-Pot Protection Strategy of Glucosamine to Assemble Building Blocks of Chitosan and Lipid A. Eur. J. Org. Chem. 2020, 2020, 5580–5595. 10.1002/ejoc.202000923. - DOI
-
- Yamada H.; Kato T.; Takahashi T. One-pot sequential glycosylation:A new method for the synthesis of branched oligosaccharides. Tetrahedron Lett. 1999, 40, 4581–4584. 10.1016/s0040-4039(99)00796-0. - DOI
-
- Kim J.-H.; Yang H.; Park J.; Boons G.-J. A General Strategy for Stereoselective Glycosylations. J. Am. Chem. Soc. 2005, 127, 12090–12097. 10.1021/ja052548h. - DOI - PubMed
- Huang X.; Huang L.; Wang H.; Ye X. . -S. Iterative One-Pot Synthesis of Oligosaccharides. Angew. Chem., Int. Ed. 2004, 43, 5221–5224. 10.1002/anie.200460176. - DOI - PubMed
-
- Oscarson S.Part 1. Chemistry of Saccharides. In Carbohydrates in Chemistry and Biology; Ernst B., Hart G. W., Sinay P., Eds.; Wiley-VCH: Weinheim, NY, 2000; Vol. 1; pp 93–116.
- SzarekKong W. A. X.Direct Halogenation of Carbohydrate Derivatives. In Preparative Carbohydrate Chemistry; Hanessian S., Ed.; Marcel Dekker, Inc.: New York, 1997; pp 105–126.
- Fairbanks A. J.; Seward C. M. P.. Synthesis and Activation of Carbohydrate Donors: Acetimidates, n-Pentenyl and Vinyl Glycosides. In Carbohydrates; Osborn H. M. I., Ed.; Academic Press: London, 2003; pp 147–194.
- Boons G.-J. Strategies in Oligosaccharide Synthesis. Tetrahedron 1996, 52, 1095–1121. 10.1016/0040-4020(95)00897-7. - DOI
- Garegg P. J. Thioglycosides as Glycosyl Donors in Oligosaccharide Synthesis. Adv. Carbohydr. Chem. Biochem. 1997, 52, 179–205. 10.1016/s0065-2318(08)60091-8. - DOI - PubMed
- Garegg P. J. Synthesis and Reactions of Glycosides. Adv. Carbohydr. Chem. Biochem. 2004, 59, 69–134. 10.1016/s0065-2318(04)59003-0. - DOI - PubMed
- Davis B. G. Recent Developments in Oligosaccharide Synthesis. J. Chem. Soc., Perkin Trans. 1 2000, 2137–2160. 10.1039/a809774g. - DOI
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