71208-20-3Relevant academic research and scientific papers
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.
Novel and efficient chemoenzymatic synthesis of D-glucose 6-phosphate and molecular modeling studies on the selective biocatalysis
Rodriguez-Perez, Tatiana,Lavandera, Ivan,Fernandez, Susana,Sanghvi, Yogesh S.,Ferrero, Miguel,Gotor, Vicente
, p. 2769 - 2778 (2008/03/13)
A concise chemoenzymatic synthesis of glucose 6-phosphate is described. Candida rugosa lipase was found to be an efficient catalyst for both regio- and stereoselective deacetylation of the primary hydroxy group in the peracetylated D-glucose. In addition, we report an improved synthesis of 1,2,3,4,6-penta-O- acetyl-α-D-glucopyranose providing a large-scale procedure for the acetylation of α-D-glucose without isomerization at the anomeric center. The high overall yield and the easy scalability makes this chemoenzymatic strategy attractive for industrial application. Furthermore, molecular modeling of phosphonate transition-state analog for the enzymatic hydrolysis step supports the substrate selectivity observed with Candida rugosa lipase. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
