Highly Water Soluble Taxol Derivatives: 7-Polyethylene Glycol Carbamates and Carbonates

Article abstract of DOI:10.1021/jo00107a010

The first examples of highly water soluble taxol derivatives (0.1 mmol/mL) were prepared by the attachement of polyethylene glycol (molecular weight 2-5 kD) at the 7-position of taxol via a urethane or carbonate linkage.When lower molecular weight polyethylene glycols (350 and 750) were used, the solubilities were considerably lower (1.87E-3 mmol/mL) but still substantially greater than taxol itself.Additional 7-subsituted taxol derivatives were also prepared by utilizing small molecules consisting of sugars and ionic and multifunctional compounds.However, most of these derivatives had solubilities, calculated from HPLC retention times, that did not differ significantly from taxol itself.The use of methoxyacetate as a protecting group during these syntheses is discussed.