ArticleBeilstein journal of organic chemistry2013
Gold-catalyzed glycosidation for the synthesis of trisaccharides by applying the armed-disarmed strategy.
Article in Beilstein journal of organic chemistry, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed, 17 citations in OpenAlex.
- Cut-insert-stitch editing reaction (CIStER) sequence for surgical chemical glycan editing.Communications chemistry · 2024Article
- AuBrBeilstein journal of organic chemistry · 2018Article
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2 authors at 1 institution in 1 country.
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Abstract
The synthesis of oligosaccharides is still a challenging task as there is no universal glycosyl donor for the synthesis of all oligosaccharides. The gold catalysis for glycosidation reactions, in which alkynylated glycosides are used, has emerged as one of the versatile options in this regard. A cleavage of the interglycosidic bond that was thought to be due to the higher reaction temperature and the acidic medium was observed during the synthesis of trisaccharides. In addition, a very little percentage of deprotection of benzyl protecting groups at the C-6 position was observed and no deprotection of benzyl ethers in aliphatic molecules was noticed. In order to overcome this fact, a collection of leaving groups that contain an alkynyl moiety were screened. It was found that 1-ethynylcyclohexanyl (Ech) glycosides are suitable for carrying out the glycosidation at 25 °C in the presence of 5 mol % each of AuCl3 and AgSbF6. Subsequently, Ech-glycosides were observed to be suitable for the synthesis of trisaccharides under gold catalysis conditions.
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