2771-57-5Relevant academic research and scientific papers
Chemical approach for the syntheses of GM4 isomers with sialic acid to non-natural linkage positions on galactose
Kurimoto, Kenta,Yamamura, Hatsuo,Miyagawa, Atsushi
, p. 39 - 50 (2015/01/08)
Cell-surface glycans containing sialic acid are involved in various biological phenomena. However, the syntheses of GM4 derivatives with (2→2) and (2→4) linkages have not been investigated to date. In this study, sialylation of all of the hydroxyl groups on galactose were investigated for the syntheses of GM4 isomers. Regioselective sialylation was achieved via protection of galactosyl acceptors using electron-rich benzyl groups. These synthetic sialylated glycans will prove to be useful tools for studying unidentified carbohydrate-mediated biological roles.
A practical synthetic method for α- and β-glycosyloxyacetic acids
Mandai, Tadakatsu,Okumoto, Hiroshi,Oshitari, Tetsuta,Nakanishi, Katsuyoshi,Mikuni, Katsuhiko,Hara, Ko-Ji,Hara, Ko-Zo
, p. 129 - 132 (2007/10/03)
Dihydroxylation of allyl 2,3,4-tri-O-benzyl-6-O-tritylglycosides provides diols, the anomers of which can easily be separated by column chromatography in a practical scale. These anomers can be cleanly transformed into α- and β-glycosyloxyacetic acids, respectively, via oxidative cleavage of the diol followed by oxidation.
Diastereoselective Bromination of Allyl Glycosides Using Tetrabutylammonium Tribromide
Bellucci, Giuseppe,Chiappe, Cinzia,D'Andrea, Felicia
, p. 221 - 230 (2007/10/02)
Both (R) and (S)-2,3-dibromo-1-propanol with e.e. up to 60percent have been obtained by diastereoselective addition of Br2 to allyl glucosides and galactosides having only one unprotected hydroxyl group at C-2 or C-6 using tetrabutylammonium tribromide, followed by hydrolysis.The absolute configuration is shown to depend on the position of the free hydroxyl and on the configuration at the anomeric centre.
