116973-12-7Relevant articles and documents
An expeditious synthesis of quercetin 3-O-β-d-glucuronide from rutin
Kajjout, Mohammed,Zemmouri, Rajae,Rolando, Christian
, p. 4738 - 4740 (2011)
We report the synthesis of the major human metabolite of quercetin, quercetin 3-O-β-d-glucuronide, from rutin (quercetin-3-rutinoside), which is commercially available at low cost. This straightforward synthesis is based on the key intermediate 3′,4′,5,7-tetra-O-benzyl-quercetin which is obtained in only two steps by the total benzylation of rutin followed by acid hydrolysis of the rutinoside residue. Glycosylation of the free 3 hydroxyl group by 1-bromo-3,4,6-tetra-O-acetyl-α-d-glucopyranoside yields the protected glucoside. TEMPO-mediated oxidation of primary alcohol on the deprotected glucoside gives access to the benzylated glucuronide. Removal of the benzyl groups which protect the quercetin hydroxyl groups by H2 (10% Pd/C) yields quercetin 3-O-β-d-glucuronide.
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.
The first synthesis of 3-O-methylcyanidin and the effect of 3-O-substitution on stability under acidic conditions
El-Meligy, Asmaa B.,Ishihara, Takehiro,Oyama, Kin-Ichi,El-Nahas, Ahmed M.,Yoshida, Kumi
, p. 946 - 959 (2019/04/26)
The simplest and most common anthocyanin in nature is 3-O-glucosylcyanidin (1), and 3-O-glucosylation is believed to stabilize the chromophore. To clarify the effect of the glucose residue we compared the stability of 1 with its aglycone, cyanidin (2), an