1192736-28-9Relevant academic research and scientific papers
Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement
Jiang, Xuefeng,Li, Jiagen,Wang, Ming
supporting information, p. 9053 - 9057 (2021/11/30)
Stereoselective glycosylation is challenging in carbohydrate chemistry. Herein, stereoselective thioglycosylation of glycals via palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside and α-sulfoxide-glucoside, respectively.
Unsaturated thioglycoside compound as well as selective synthesis method and application thereof
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Paragraph 0195-0198, (2021/11/19)
The invention discloses a synthesis method for selectively synthesizing an alpha-thioglycoside compound as shown in a formula (II) and a beta-thioglycoside compound as shown in a formula (III), which comprises the following steps: in a reaction solvent, by taking triacetyl glucose alkene as a reaction raw material and organic thiosulfates with different substituent groups as a sulfur source, under the action of a metal palladium salt and a ligand, selectively synthesizing an alpha-thioglycoside compound (II) and a beta-thioglycoside compound (III). The synthesis method provided by the invention has the advantages of easily available and cheap raw materials, simple reaction operation, mild reaction conditions, high yield and excellent functional group tolerance. According to the invention, synthesis and modification of some complex molecules are realized, and an efficient method for selectively constructing the thioglycoside compound containing the unsaturated bond is provided for research of pharmaceutical chemistry.
Scope of AuCl3 in the activation of per-O-acetylglycals
Balamurugan, Rengarajan,Koppolu, Srinivasa Rao
experimental part, p. 8139 - 8142 (2009/12/09)
Gold(III)chloride in catalytic amounts activates 3,4,6-tri-O-acetyl-d-glucal, 3,4,6-tri-O-acetyl-d-galactal, and 3,4-di-O-acetyl-l-rhamnal efficiently. The activated species can be employed in the Ferrier reaction with different nucleophiles at ambient conditions. Attempts have been made to make β-anomer of the Ferrier product from anomeric-O-propargylated Ferrier product.
