ArticleAngewandte Chemie (International ed. in English)2015
The isothiocyanato moiety: an ideal protecting group for the stereoselective synthesis of sialic acid glycosides and subsequent diversification.
Article in Angewandte Chemie (International ed. in English), 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed, 37 citations in OpenAlex.
- Recent Advances in Chemical Synthesis of Amino Sugars.Molecules (Basel, Switzerland) · 2023Review
- Biocatalysis versus Molecular Recognition in Sialoside-Selective Neuraminidase Biosensing.ACS chemical biology · 2023Article
- Diacetyl strategy for synthesis of NHAc containing glycans: enhancing glycosylation reactivity via diacetyl imide protection.Frontiers in chemistry · 2023Review
- Influence of protecting groups on O- and C-glycosylation with neuraminyl and ulosonyl dibutylphosphates.Carbohydrate research · 2020Article
- Synthesis and Stereocontrolled Equatorially Selective Glycosylation Reactions of a Pseudaminic Acid Donor: Importance of the Side-Chain Conformation and Regioselective Reduction of Azide Protecting Groups.Journal of the American Chemical Society · 2018Article
- Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges.Chemical reviews · 2018Review
- Facile and robust methods for the regioselective acylation of N-acetylneuraminic acid.New journal of chemistry = Nouveau journal de chimie · 2018Article
- Article
- Stereoselective Synthesis of 5-epi-α-Sialosides Related to the Pseudaminic Acid Glycosides. Reassessment of the Stereoselectivity of the 5-Azido-5-deacetamidosialyl Thioglycosides and Use of Triflate as Nucleophile in the Zbiral Deamination of Sialic Acids.The Journal of organic chemistry · 2016Article
- Automated solid-phase synthesis of oligosaccharides containing sialic acids.Beilstein journal of organic chemistry · 2015Article
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
The preparation of a crystalline, peracetyl adamantanyl thiosialoside donor protected by an isothiocyanate group is described. On activation at -78 °C in the presence of typical carbohydrate acceptors, this donor gives high yields of the corresponding sialosides with exquisite α-selectivity. The high selectivity extends to the 4-O-benzyl-protected 3-OH acceptors, which are typically less reactive and selective than galactose 3,4-diols. Treatment of the α-sialosides with tris(trimethylsilyl)silane or allyltris(trimethylsilyl)silane results in replacement of the C5-N5 bond by a C-H or a C-C bond. The reaction of the isothiocyanate-protected sialosides with thioacids generates amides, while reaction with an amine gives a thiourea, which can be converted into a guanidine. The very high α-selectivities observed with the new donor and the rich chemistry of the isothiocyante function considerably extend the scope for optimization at the sialoside 5-position.
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