67540-18-5Relevant academic research and scientific papers
C -Glycosylation enabled by N -(glycosyloxy)acetamides
Li, Bo-Han,Li, Tian,Liu, Meng,Liu, Miao,Wu, Xia,Xiong, De-Cai,Ye, Xin-Shan
supporting information, p. 3043 - 3046 (2020/05/08)
The C-glycosylation of C-nucleophiles including allyltrimethylsilane, silyl enol ethers and phenols with N-(glycosyloxy)acetamides as glycosyl donors has been realized. This protocol provides a convenient and practical route for the synthesis of alkyl C-glycosides and aryl 2-deoxy-β-C-glycosides under mild reaction conditions.
Copper-mediated O-arylation of lactols with aryl boronic acids
Sui, Jing-Jing,Xiong, De-Cai,Ye, Xin-Shan
supporting information, p. 1533 - 1537 (2019/06/21)
An efficient and novel methodology to access phenolic glycosides has been established by using copper-mediated coupling reaction of aryl boronic acids with hemiacetals. The reaction takes place normally in the presence of Cu(OAc)2 (1.0 equiv.) and pyridine (2.0 equiv.) at 40 °C. This protocol distinguishes itself by wide substrate scope, operational simplicity and giving rise to a myriad of phenolic glycosides in good to excellent yields.
Application of silver N-heterocyclic carbene complexes in O-glycosidation reactions
Talisman, Ian J.,Kumar, Vineet,Deschamps, Jeffrey R.,Frisch, Mark,Malhotra, Sanjay V.
experimental part, p. 2337 - 2341 (2011/12/04)
We report the efficient O-glycosidation of glycosyl bromides with therapeutically relevant acceptors facilitated by silver N-heterocyclic carbene (Ag-NHC) complexes. A set of four Ag-NHC complexes was synthesized and evaluated as promoters for glycosidation reactions. Two new bis-Ag-NHC complexes derived from ionic liquids 1-benzyl-3-methyl-1H-imidazolium chloride and 1-(2-methoxyethyl)-3-methylimidazolium chloride were found to efficiently promote glycosidation, whereas known mono-Ag complexes of 1,3-bis(2,4,6- trimethylphenyl)imidazolium chloride and 1,3-bis(2,6-di-isopropylphenyl) imidazolium chloride failed to facilitate the reaction. The structures of the promoters were established by X-ray crystallography and these complexes were employed in the glycosidation of different glycosyl bromide donors with biologically valuable acceptors, such as estrone, estradiol, and various flavones. The products were obtained in yields considered good to excellent, and all reactions were highly selective for the β isomer regardless of neighboring group effects.
Metallocene bis(perfluoroalkanesulfonate)s as air-stable cationic Lewis acids
Qiu, Renhua,Zhang, Guoping,Xu, Xinhua,Zou, Kangbin,Shao, Lingling,Fang, Dawei,Li, Yinhui,Orita, Akihiro,Saijo, Ryosuke,Mineyama, Hidetaka,Suenobu, Tomoyoshi,Fukuzumi, Shunichi,An, Delie,Otera, Junzo
experimental part, p. 1524 - 1528 (2009/09/06)
Zirconocene and titanocene bis(perfluorooctanesulfonate)s were synthesized. In contrast to the corresponding triflates and perchlorates, these compounds are air- and water-stable. They were proved to be ionic on the basis of conductivity measurements and X-ray analysis, allowing these complexes to be stored for months. The strong Lewis acidity of these cationic metallocene species, which was proved by ESR study, enabled catalytic glycosylation.
Catalytic glycosylation with rhodium(III)-triphos catalysts
Wagner, Beatrice,Heneghan, Michael,Schnabel, Gerhard,Ernst, Beat
, p. 1303 - 1306 (2007/10/03)
The formation of glycosides in high yield from 1-hydroxy sugars using catalytic amounts (0.5molpercent) of Rh(III)Cl3(triphos) (1a) or [Rh(III)(MeCN)3(triphos)](TfO)3 (1b) is described. High stereocontrol at the anomeric c
O-Glycoside Synthesis under Neutral Conditions in Concentrated Solutions of LiClO4 in Organic Solvents Employing Benzyl-Protected Glycosyl Donors
Boehm, Gerd,Waldmann, Herbert
, p. 613 - 620 (2007/10/03)
The benzyl-protectd glucosyl trichloroacetimidates, phosphates, and halides 1 are activated under neutral conditions and without the addition of any further promoter in 1 M solutions of LiCl4 in ether, CH2Cl2, CHCl3, or CH3CN and react under these conditi
New Synthetic Methods and Reagents for Complex Carbohydrates. IX. Aryl D-Glucopyranosides and 1-Aryl-1-deoxy-D-glucopyranoses from 2,3,4,6-Tetra-O-benzyl-α-D-glucopyranosyl Dimethylphosphinothioate
Yamanoi, takashi,Fujioka, Ayumi,Inazu, Toshiyuki
, p. 1488 - 1491 (2007/10/02)
The reactions of 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl dimethylphosphinothioate and phenolic compounds gave the corresponding aryl α-D-glucopyranosides predominantly in good yields, even when the trimethylsiloxy derivatives of benzene, which are known
Aryl C-glycosides from O-glycosyltrichloroacetimidates and phenol derivatives with trimethylsilyl trifluoromethanesulfonate (TMSOTf) as the catalyst
Mahling,Schmidt
, p. 325 - 328 (2007/10/02)
The reaction of O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)trichloracetimidate (1), as glycosyl donor with phenol and naphthol derivatives 2a-d and 2f-h, as glycosyl acceptors, furnished in the presence of catalytic amounts of TMSOTf the corresponding o-hydroxyaryl C-β-D-glucopyranosides 3a-d, f-h regio- and stereoselectively. The less reactive 4-methoxyphenol (2e), α-naphthol (2i), the hydroxy substituted coumarines 2j, k and the flavone 2l afforded under these conditions O-glycosides 5e, i-l. Hydrogenolytic O-debenzylation of 3a,b,d afforded compounds 4a,b,d.
