A Facile Method for β-Selenoglycoside Synthesis Using β-p-Methylbenzoyl Selenoglycoside as the Selenating Unit

Abstract

[reaction: see text] The reaction between alpha-glycosyl bromides and potassium p-methylselenobenzoate yields beta-p-methylbenzoyl selenoglycosides. The acyl selenoglycosides were activated by the action of a secondary amine and Cs2CO3 to produce an anomeric selenolate anion, which reacted in situ with various electrophiles to yield novel selenoglycosides while retaining the anomeric stereochemistry.

Antinociceptive and anti-hyperalgesic effects of bis(4-methylbenzoyl) diselenide in mice: Evidence for the mechanism of action

“…Drugs bis(4-Methylbenzoyl) diselenide (Figure 1) was prepared and characterized as previously described (Kawai et al, 2005). The 1 H NMR and 13 C NMR spectra were in full agreement with its assigned structure.…”

Regulation of Melanin Synthesis by Selenium-Containing Carbohydrates

“…[15][16][17][18] And we previously reported that selenazole derivatives can inhibit the mushroom tyrosinase. 19) Selenoglycoside (SG) series have been recently developed as a series of selenium-containing carbohydrates 20) (Fig. 1).…”

Convergent synthesis of the pentasaccharide repeating unit of the O-antigenic polysaccharide of enterohaemorrhagic Escherichia coli O113

“…A disaccharide glycosyl acceptor (7) was stereoselectively condensed with a trisaccharide glycosyl donor (12). The disaccharide derivative (7) and the trisaccharide derivative (12) were prepared from suitably protected monosaccharide intermediates 2 [12], 3 [13], 4 [14], 5 [15] and 6 [16] prepared from the commercially available reducing sugars using reported literature (Fig. 2).…”