121570-33-0Relevant articles and documents
Avoiding pyran ring opening during palladium acetate catalyzed C-glycosidation of peracetylated glycals
De La Figuera, Natalia,Forns, Pilar,Fernàndez, Joan-Carles,Fiol, Sandra,Fernández-Forner, Dolors,Albericio, Fernando
, p. 7271 - 7274 (2005)
Palladium acetate catalyzed C-glycosidation of peracetylated glycals with arylboronic acids in acetonitrile (CH3CN) yields the desired 1-substituted 2,3-unsaturated glycal as well as a byproduct corresponding to the ring-opened pyran, present in varying proportions depending on the reaction conditions used. The byproduct is not formed when toluene/EtOH is used as reaction solvent.
Palladium(ii)-catalyzed stereoselective synthesis of: C-glycosides from glycals with diaryliodonium salts
Das, Mrinmoy,Lee, Jiande,Liu, Xue-Wei,Pal, Kumar Bhaskar
, p. 2242 - 2251 (2020/04/07)
An efficient palladium(ii) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-Aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of
Desulfitative C-arylation of glycals by using benzenesulfonyl chlorides
Kusunuru, Anil Kumar,Yousuf, Syed Khalid,Tatina, Madhubabu,Mukherjee, Debaraj
, p. 459 - 462 (2015/01/30)
The palladium-catalyzed stereoselective synthesis of 2,3-deoxy-C-aryl glycosides was investigated. The strategy is based on the Pd-catalyzed desulfitative Heck coupling of arylsulfonyl chlorides and glycals with good leaving groups. An attempt was made to
Asymmetric synthesis of (-)-6-epi-centrolobine
Reddy, Chada Raji,Madhavi, Pasupulety Phani,Chandrasekhar, Srivari
experimental part, p. 2939 - 2942 (2009/04/07)
A stereoselective total synthesis of (-)-6-epi-centrolobine, an unnatural analogue of (-)-centrolobine, starting from readily available tri-O-acetyl-D-glucal has been described for the first time. The key steps involved in this synthetic approach are stereoselective C-glycosidation, dehydroxylation and Wittig reaction. The target molecule was achieved in nine steps with 49% overall yield. Georg Thieme Verlag Stuttgart.
Synthesis of C-aryl-Δ2,3-glycopyranosides via uncatalyzed addition of triarylindium reagents to glycals
Price, Sarah,Edwards, Stephen,Wu, Tiffany,Minehan, Thomas
, p. 5197 - 5201 (2007/10/03)
2,3-Unsaturated-C-aryl glycopyranosides are important intermediates in the synthesis of medicinally important C-aryl glycosides. Treatment of glycal acetates with triarylindiums in ether at room temperature gives good yields of C-aryl-Δ2,3-glyc
Molybdenum-catalyzed allylic substitution in glycals: A C-C bond-forming Ferrier-type reaction
Malkov, Andrei V.,Farn, Benjamin P.,Hussain, Nigel,Kocovsky, Pavel
, p. 1735 - 1745 (2007/10/03)
The mild, Lewis-acidic complexes [Mo(CO)4Br2]2, (MeCN)2Mo(CO)3(SnCl3)Cl, and (acac)2Mo(OTf)2 have been found to catalyze the C(1)-specific C-glycosylation reaction of glycal acetates 1-3 with silyl enol ethers 4a-4c and electron-rich aromatics 5a, 5b (PhOMe, PhOH). While silyl enol ethers produce predominantly α-C-glycopyranosides (with 2 : 1 to 4 : 1 selectivity), aromatics tend to afford mainly β-C-glycopyranosides (2 : 1 to 3 : 1) in a thermodynamically controlled process.
Palladium(II) Acetate Catalyzed Stereoselective C-Glycosidation of Peracetylated Glycals with Arylboronic Acids
Ramnauth, Jailall,Poulin, Odile,Rakhit, Suman,Maddaford, Shawn P.
, p. 2013 - 2014 (2007/10/03)
(matrix presented) Addition of a variety of arylboronic acids to peracetylated glycals takes place in the presence of a catalytic amount of Pd(OAc)2. The reaction involves the syn addition of a σ-aryl-Pd complex to the glycal double bond followed by anti elimination of Pd(OAc)2 to provide a carbon-Ferrier type product. This method provides a practical and convenient stereoselective synthesis of C-arylglycosides.
Reinvestigation of Phenolic Ferrier Reaction: Selective Synthesis of Aryl O-Δ2-Glycosides
Noshita, Toshiro,Sugiyama, Takeyoshi,Kitazumi, Yoshiharu,Oritani, Takayuki
, p. 2052 - 2055 (2007/10/02)
Reinvestigation of the phenolic Ferrier reaction is described.Ferrier reaction between acetylglycals and phenols in toluene in the presence of a catalytic amount of lewis acid at low temperature gave aryl O-Δ2-glycosides in moderate to good yie
Phenolic ferrier reaction and its application to the natural product synthesis
Noshita, Toshiro,Sugiyama, Takeyoshi,Kitazumi, Yoshiharu,Oritani, Takayuki
, p. 8259 - 8262 (2007/10/02)
Ferrier reaction between acetylglycals and phenols proceeded smoothly to give α-O-Δ2 glycosides predominantly. The products were converted to bio-active natural products.
Electrophilic Substitution of Aromatic Compounds by Unsaturated Sugar Derivatives
Grynkiewicz, Grzegorz,Zamojski, Aleksander
, p. 1024 - 1027 (2007/10/02)
Glycals 1 and 2 react with methoxybenzene in the presence of SnCl2 forming p-substituted C-glycosyl compounds 4 and 5 + 6 respectively.Under similar conditions 1-O-benzoyl- or methyl pent-2-enopyranos-4-uloses (7) and (8) react with electron rich aromatic
