ArticleJournal of carbohydrate chemistry
Exploration of the Oxazolidinthione Protecting System for the Synthesis of Sialic Acid Glycosides.
Article in Journal of carbohydrate chemistry. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 4 papers.
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Who cites it
4 citing papers in PubMed, 11 citations in OpenAlex.
- Influence of protecting groups on O- and C-glycosylation with neuraminyl and ulosonyl dibutylphosphates.Carbohydrate research · 2020Article
- Article
- The isothiocyanato moiety: an ideal protecting group for the stereoselective synthesis of sialic acid glycosides and subsequent diversification.Angewandte Chemie (International ed. in English) · 2015Article
- Influence of side chain conformation and configuration on glycosyl donor reactivity and selectivity as illustrated by sialic acid donors epimeric at the 7-position.Journal of the American Chemical Society · 2013Article
Corrections and comments
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
An N-acetyl oxazolidinthione protected sialyl thioglycoside was synthesized and its use as a sialyl donor studied. The strongly electron-withdrawing nature of the oxazolidinthione moiety is such that activation could not be achieved at -78 °C. Couplings were therefore conducted at the lowest convenient temperature (-50 °C). Glycosides were formed in good yield but in two out three cases studied selectivities were lower than those seen with the corresponding N-acetyl oxazoldinone protected donor. The resulting N-acetyl oxazolidinthione protectd disaccharides were converted to the corresponding N-acetyl oxazolidinones by treatment with N-iodosuccinimide and triflic acid in the presence of water at 0 °C.
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Registered trials
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