93414-73-4Relevant academic research and scientific papers
Nickel-catalyzed reductive coupling of glucosyl halides with aryl/vinyl halides enabling β-selective preparation of C-aryl/vinyl glucosides
Liu, Jiandong,Lei, Chuanhu,Gong, Hegui
, p. 1492 - 1496 (2019/07/05)
This work describes stereoselective preparation of β-C-aryl/vinyl glucosides via mild Ni-catalyzed reductive arylation and vinylation of C1-glucosyl halides with aryl and vinyl halides. A broad range of aryl halides and vinyl halides were employed to yield C-aryl/vinyl glucosides in 42%–93% yields. Good to excellent β-selectivities were obtained for C-glucosides by using tridentate ligand.
Glycosyl Cross-Coupling with Diaryliodonium Salts: Access to Aryl C -Glycosides of Biomedical Relevance
Yi, Duk,Zhu, Feng,Walczak, Maciej A.
, p. 1936 - 1940 (2018/04/12)
A stereospecific cross-coupling reaction of anomeric nucleophiles with diaryliodonium triflates resulting in the synthesis of aryl C-glycosides is reported. This process capitalizes on a stereoretentive reaction of configurationally stable C1 stannanes and is promoted by a palladium catalyst in the presence of a bulky phosphine ligand that suppresses the undesired β-elimination. The utility of this reaction has been demonstrated in the preparation of a series of C-glycosides derived from common saccharides resulting in exclusive transfer of anomeric configuration from the anomeric nucleophile to the product, and in the synthesis of empagliflozin, a commercial antidiabetic drug.
Convenient Synthesis of C-β-D-Glucopyranosyl Arenes - Synthesis of 5,7,4'-Tri-O-methylvitexin
Frick, Wendelin,Schmidt, Richard R.
, p. 565 - 570 (2007/10/02)
Reaction of the C-lithiated phenol and flavanon derivatives 4a-, b-A and 16-A with the ring-open, O-benzyl-protected D-glucoses 3 and 11 furnishes the corresponding C-glucosyl derivatives 5a,b, 12, and 19, respectively, in good yields.Hydrogenolytic deben
STUDIES ON C-GLYCOSIDES. XIII. C-GLUCOSIDES FROM O-GLUCOSYL 3,5-DINITRO BENZOATE
Cai, Meng-Shen,Qiu, Dong-Xu
, p. 851 - 856 (2007/10/02)
From O-glucopyranosyl 3,5-dinitro benzoate (1) and aryl ethers C-glucosides were obtained stereoselectively in the presence of Lewis acid in high yield.In most cases, the β-anomer was formed.
The First Direct Method for C-Glucopyranosyl Derivatization of 2,3,4,6-Tetra-O-benzyl-D-glucopyranose
Allevi, Pietro,Anastasia, Mario,Ciuffreda, Pierangela,Fiecchi, Alberto,Scala, Antonio
, p. 1245 - 1246 (2007/10/02)
Commercially available 2,3,4,6-tetra-O-benzyl-D-glucopyranose, activated by trifluoroacetic anhydride reacts, in the presence of Lewis acids, with various silyl enol ethers or with allylsilane to yield C-D-glucopyranosyl derivatives of the α-configuration
Aromatic and heterocyclic 1-C-substituted derivatives of 1,5-anhydro-D-glucitol.
Grynkiewicz,BeMiller
, p. 273 - 276 (2007/10/02)
Reaction of anomeric 1-O-acyl and 1-halide derivatives of 2,3,4,6-tetra-O-benzyl-D-glucose with anisole, ferrocene, thiophene, furan, and 1,3,5-trimethoxybenzene in the presence of a Lewis acid gives the corresponding C-beta-D-glucopyranosyl derivatives.
