Polysialosides scaffolded on p-tert-butylcalix[4]arene

Article abstract of DOI:10.1016/0040-4039(96)01167-7

p-Tert-butylcalix[4]arene (1) was transformed into known tetraethyl ester 2 to provide cone-shaped calix[4]arene used for the scaffolding of tetravalent α-sialoside. Ester 2 was transformed into acid chloride 4 which after treatment with mono-Boc-1,4-butanediamine, trifluoroacetolysis and N-chloroacetylation afforded tetraamine 7. Conjugation of α-thiosialoside 9 by nucleophilic substitution and deprotection furnished water-soluble tetravalent α-thiosialoside 12 which bound strongly to the plant lectin wheat germ agglutinin.