POLYSIALOSIDES SCAFFOLDED ON P-TERT-BUTYLCALIX[4]ARENE

p-Tert-butylcalix[4]arene (1) was transformed into known tetraethyl es ter 2 to provide cone-shaped calix[4]arene used for the scaffolding of tetravalent alpha-sialoside. Ester 2 was transformed into acid chlori de 4 which after treatment with mono-Boc-1,4-butanediamine, trifluoroa cetolysis and N-chloroacetylation afforded tetraamine 7, Conjugation o f alpha-thiosialoside 9 by nucleophilic substitution and deprotection furnished water-soluble tetravalent alpha-thiosialoside 12 which bound strongly to the plant lectin wheat germ agglutinin. Copyright (C) 199 6 Elsevier Science Ltd