Sugar conjugates of fulvestrant (ICI 182,780): Efficient general procedures for glycosylation of the fulvestrant core

Article abstract of DOI:10.1016/j.tetlet.2003.11.140

We have prepared glucose and cellobiose conjugates at the phenolic 3- and hydroxylic 17-positions of the pure anti-estrogenic compound fulvestrant (ICI 182,780), which has recently been approved in the USA for the treatment of advanced postmenopausal breast cancer. Glycosylation at the 17-position was achieved most effectively using pivaloyl protection of the sugar imidates employed, which we found suppressed the competing transacylation reaction and led to improved yields of the product glycosides.