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

Hiroki Hamada , Hatsuyuki Hamada, Kei Shimoda , Tadakatsu Mandai, Kohji Ishihara, Yuya Kiriake and Atsuhito Kuboki

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 chromatog. 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.                                                                                                                                                               
           

Natural Product Communications

Sage Journals

16

9

1

3