Protecting groups for glucuronic acid: application to the synthesis of new paclitaxel (taxol) derivatives.
To prepare two new glucuronide conjugates, allyl ester and allyl carbonates were used as protecting groups of the glucuronic moiety. In this way, an aniline glycosyl carbamate spacer linked to the 2'-OH of paclitaxel was obtained. By using palladium chemistry, an efficient one-step removal of all the allyl groups at the end of the synthesis afforded the desired compounds in good yields.
El Alaoui
Abdessamad
A
UMR 176 CNRS/Institut Curie, Centre de Recherche, 26 rue d'Ulm, 75248 Paris Cedex 05, France.
Schmidt
Frédéric
F
Monneret
Claude
C
Florent
Jean-Claude
JC
D020723:Glucuronic Acid / Q000737:chemistry*; D015394:Molecular Structure; D017239:Paclitaxel / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013997:Time Factors
D020723:Glucuronic Acid; D017239:Paclitaxel