Literature DB >> 17168579

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

Abdessamad El Alaoui1, Frédéric Schmidt, Claude Monneret, Jean-Claude Florent.   

Abstract

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.

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Year:  2006        PMID: 17168579     DOI: 10.1021/jo0612675

Source DB:  PubMed          Journal:  J Org Chem        ISSN: 0022-3263            Impact factor:   4.354


  5 in total

1.  Ultrasound-directed enzyme-prodrug therapy (UDEPT) using self-immolative doxorubicin derivatives.

Authors:  Karolin Roemhild; Helena C Besse; Bi Wang; Quim Peña; Qingxue Sun; Daiki Omata; Burcin Ozbakir; Clemens Bos; Hans W Scheeren; Gert Storm; Josbert M Metselaar; Haijun Yu; Ruth Knüchel-Clarke; Fabian Kiessling; Chrit T W Moonen; Roel Deckers; Yang Shi; Twan Lammers
Journal:  Theranostics       Date:  2022-06-06       Impact factor: 11.600

Review 2.  The Therapeutic Potential of Migrastatin-Core Analogs for the Treatment of Metastatic Cancer.

Authors:  Ernest Giralt; Daniele Lo Re
Journal:  Molecules       Date:  2017-02-09       Impact factor: 4.411

3.  Comparing the immunogenicity of glycosidase-directed resiquimod prodrugs mediated by cancer cell metabolism.

Authors:  Austin T Ryan; Anunay J Pulukuri; Maryam Davaritouchaee; Armina Abbasi; Aaron T Hendricksen; Larissa K Opp; Anthony J Burt; Amy E Nielsen; Rock J Mancini
Journal:  Acta Pharmacol Sin       Date:  2020-05-25       Impact factor: 6.150

Review 4.  Design, synthesis and applications of hyaluronic acid-paclitaxel bioconjugates.

Authors:  Francesca Leonelli; Angela La Bella; Luisa Maria Migneco; Rinaldo Marini Bettolo
Journal:  Molecules       Date:  2008-02-12       Impact factor: 4.411

5.  Chloromethyl Glycosides as Versatile Synthons to Prepare Glycosyloxymethyl-Prodrugs.

Authors:  Hidde Elferink; Willem H C Titulaer; Maik G N Derks; Gerrit H Veeneman; Floris P J T Rutjes; Thomas J Boltje
Journal:  Chemistry       Date:  2022-01-24       Impact factor: 5.020

  5 in total

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