US EPA

7436881 

Journal Article 

Protecting groups for glucuronic acid: application to the synthesis of new paclitaxel (taxol) derivatives 

El Alaoui, A; Schmidt, F; Monneret, C; Florent, JC 

2006 

Yes 

Journal of Organic Chemistry
ISSN: 0022-3263
EISSN: 1520-6904 

71 

26 

9628-9636 

English 

17168579 

10.1021/jo0612675 

WOS:000242845500009 

https://www.scopus.com/inward/record.uri?eid=2-s2.0-33845927384&doi=10.1021%2fjo0612675&partnerID=40&md5=fec58096f5a854a87b2aa7fd4cf449aa
Exit
 

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. 

Carbamate spacers; Glucuronic acid; Glucuronic moieties; Glucuronide conjugates; Alcohols; Carbonates; Derivatives; Synthesis (chemical); Carboxylic acids; 2' o (n beta dextro glucopyranosylcarbamoyl 4 oxy)benzyloxycarbonylpaclitaxel; allyl compound; carbamic acid; carbonic acid; carbonyl derivative; ester derivative; glucuronic acid; glucuronide; o [[n (beta dextro glucopyranosyl)carbamoyl 4 oxy]benzyloxycarbonyl] 2 aminoethyloxycarbonylpaclitaxel; paclitaxel derivative; palladium; prodrug; unclassified drug; article; conjugate; deprotection reaction; drug cytotoxicity; drug decomposition; drug synthesis; high performance liquid chromatography; human; human cell; IC 50; quantum yield; reaction analysis; structure activity relation; Glucuronic Acid; Molecular Structure; Paclitaxel; Stereoisomerism; Time Factors