ArticleScience China. Chemistry2011
Pre-activation based stereoselective glycosylations: Stereochemical control by additives and solvent.
Article in Science China. Chemistry, 2011. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 6 papers.
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Who cites it
6 citing papers in PubMed, 26 citations in OpenAlex.
- Article
- Convergent chemoenzymatic synthesis ofChemical science · 2023Article
- Additive-controlled asymmetric iodocyclization enables enantioselective access to both α- and β-nucleosides.Nature communications · 2023Article
- Gold-catalyzed synthesis of α-D-glucosides using an o-ethynylphenyl β-D-1-thioglucoside donor.Carbohydrate research · 2019Article
- Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.Chemical reviews · 2018Review
- Chemical Synthesis of the Repeating Unit of Type V Group B Streptococcus Capsular Polysaccharide.Organic letters · 2016Article
Corrections and comments
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Authors and funding
3 authors at 1 institution in 1 country.
Funding
Abstract
Stereochemical control is an important issue in carbohydrate synthesis. Glycosyl donors with participating acyl protective groups on 2-O have been shown to give 1,2-trans glycosides reliably under the pre-activation based reaction condition. In this work, the effects of additives and reaction solvents on stereoselectivity were examined using donors without participating protective groups on 2-O. While several triflate salt additives did not have major effects, the amount of AgOTf was found to significantly impact the reaction outcome. Excess AgOTf led to lower stereochemical control presumably due to its coordination with the glycosyl triflate intermediate and a more S(N)1 like reaction pathway. In contrast, the stereoselectivity could be directed by reaction solvents, with diethyl ether favoring the formation of α glycosides and dichloromethane leading to β isomers. The trend of stereochemical dependence on reaction solvent was applicable to a variety of building blocks including the selective formation of β-mannosides.
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Registered trials
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