Synthesis of Ester-Linked Paclitaxel-Glycoside Conjugate as a Water-Soluble Paclitaxel Derivative—Maltoside Modification of Paclitaxel through Ester-Linker (Ester-Spacer)

Abstract

To synthesize a water-soluble paclitaxel derivative, the anomers of diols of allyl 2,3,4-tri- O-benzyl-6- O-tritylglycoside (maltoside) were prepared, which can be separated by chromatographic procedure. One anomer was converted into α-glycosyloxyacetic acid (maltosyloxyacetic acid) by oxidative cleavage of the diol and subsequent oxidation. Ester-linked paclitaxel-glycoside conjugate, 7-glycolylpaclitaxel 2″- O-α-maltoside, was provided by condensation of 2′-TES paclitaxel with α-glycosyloxyacetic acid (maltosyloxyacetic acid) followed by deprotection of hydroxy groups.