643741-20-2Relevant academic research and scientific papers
Preparation of sialyl donors carrying functionalized ester substituents: Effects on the selectivity of glycosylation
Ishiwata, Akihiro,Ito, Yukishige
, p. 1339 - 1343 (2003)
Methylthio sialyl donors having various ester substituents were prepared systematically. Nucleophilic displacement of methyl ester with Ph3SiSH and Cs2C3 followed by in situ alkylation with RX or esterification with R-OH/DCC afforded these compounds in good yields. Glycosylations promoted by NIS-TfOH were examined in order to examine the effect of substituent of the ester portion. When conducted in CH3CN, enhanced α-selectivities were observed for cyanomethyl, 2-cyanoethyl, 2-cyanobenzyl, and 2-nitrobenzyl esters, implying that these substituents are effective enhancing the solvent effect of acetonitrile, possibly by stabilizing the β-oriented nitrilium ion.
