1365092-15-4Relevant academic research and scientific papers
Synthesis of Diverse C2-Glyco-Acyl Azides and -Ureas by Palladium-Catalyzed Carbonylation Coupling of 2-Iodoglycals
Soares-Paulino, Ant?nio Augusto,Stefani, Hélio A.
, (2020)
Herein, we describe the synthesis of acyl azides and acyl urea glycals, a new class of C-2 branched glycoconjugates, employing Pd-catalyzed carbonylative coupling. A new strategy was developed to obtain acyl azides by carbonylative coupling between 2-iodo-glycals and NaN3 catalyzed by Pd(dba)2/Xantphos and carbon monoxide as a carbonyl source. Acyl azide glycals were used as synthetic intermediates in obtaining new acyl urea glycals via carbonylative coupling catalyzed by Pd(OAc)2 and 1,10-Phen. Different glycal substrates, including disaccharide-type, were studied, and various acyl azides and acyl ureas were prepared. Reaction yields were moderate to high (31–99 %) and reaction time varying from short to long (0.5–20 h).
α,β-Unsaturated 2-Ketoglycosides via Pd-Catalyzed Carbonylative Heck Reaction of 2-Iodoglycals
Darbem, Mariana P.,Esteves, Henrique A.,de Oliveira, Isadora M.,Stefani, Hélio A.
, p. 5220 - 5226 (2020)
The synthesis of C-glycosides is of great importance in the field of carbohydrate chemistry given its ubiquity in biologically active molecules. Herein, we describe a protocol for the Pd-catalyzed carbonylative Heck reaction of activated olefins and 2-iod
Carbonylative Negishi-Type Coupling of 2-Iodoglycals with Alkyl and Aryl Halides
Esteves, Henrique A.,Darbem, Mariana P.,Pimenta, Daniel C.,Stefani, Hélio A.
, p. 7384 - 7388 (2019)
C-Glycosides are valuable organic compounds in the field of medicinal chemistry due to their ubiquity inside living systems and pronounced biological activity. Herein, we describe an approach to alkyl-ketones bearing glycal units via the Pd-catalyzed carb
Access to: C -aryl/alkenylglycosides by directed Pd-catalyzed C-H functionalisation of the anomeric position in glycal-type substrates
De Robichon, Morgane,Bordessa, Andrea,Malinowski, Maciej,Uziel, Jacques,Lubin-Germain, Nadège,Ferry, Angélique
, p. 11806 - 11808 (2019)
Directed palladium-catalyzed C-H functionalisation of C2-amido glycals onto the anomeric position is described as a novel route to C-aryl/alkenylglycosides. An aminoquinoline-type directing group was used to successfully introduce diverse (hetero)aryl and alkenyl groups at position 1 of the sugar (20 examples). Its application to the synthesis of a dapagliflozin analogue is presented.
Access to Complex C2-Branched Glycoconjugates via Palladium-Catalyzed Aminocarbonylation Reaction of 2-Iodoglycals
Bordessa, Andrea,Ferry, Angélique,Lubin-Germain, Nadège
, p. 12459 - 12465 (2016)
A convenient and straightforward synthesis of 2-amidoglycals through a palladium-catalyzed aminocarbonylation reaction between 2-iodoglycal partners and diverse amines in the presence of a “CO” source has been developed. Several amines such as aliphatics,
N -Halosuccinimide/AgNO3-efficient reagent systems for one-step synthesis of 2-haloglycals from glycals: Application in the synthesis of 2C-branched sugars via heck coupling reactions
Dharuman, Suresh,Vankar, Yashwant D.
supporting information, p. 1172 - 1175 (2014/03/21)
An expedient one-step synthesis of 2-iodoglycals and 2-bromoglycals from glycals using NIS/AgNO3 and NBS/AgNO3 as reagent systems has been developed. The utility of these 2-haloglycals has been demonstrated by converting them into 2C
Phosphine-free suzuki-miyaura cross-coupling in aqueous media enables access to 2-C-aryl-glycosides
Cobo, Isidro,Matheu, M. Isabel,Castillon, Sergio,Boutureira, Omar,Davis, Benjamin G.
supporting information; experimental part, p. 1728 - 1731 (2012/06/18)
A general strategy for the synthesis of 2-aryl-glycals and their elaboration to 2-C-aryl-α-glycosides and 1,5-anhydro-2-C-aryl-2-deoxy alditols are described. The use of reliable, efficient phosphine-free Suzuki-Miyaura cross-coupling of 2-iodoglycals in
