𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Mechanistic considerations pertaining to the solvolysis of paclitaxel analogs bearing ester groups at the C2′ position

✍ Scribed by Wieslaw A Klis; Jeffrey G Sarver; Paul W Erhardt

Book ID
104231691
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
76 KB
Volume
42
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Dilute solutions of paclitaxel-related derivatives having chloroacetyl esters in the C2% position undergo ready methanolysis according to pseudo first-order kinetics while more concentrated solutions appear to be stabilized, possibly by the formation of hydrophobic aggregates that tend to bury this reaction center. Methanolysis is also attenuated in the presence of weak acid, suggesting that paclitaxel's neighboring benzamide nitrogen may be participating in the reaction by serving as an assisting nucleophile.

📜 SIMILAR VOLUMES

Corrigendum to “Mechanistic consideratio
Corrigendum to “Mechanistic considerations pertaining to the solvolysis of paclitaxel analogs bearing ester groups at the C2′ position”: [Tetrahedron Lett. 42 (2001) 7747]
✍ Wieslaw A. Klis; Jeffrey G. Sarver; Paul W. Erhardt 📂 Article 📅 2003 🏛 Elsevier Science 🌐 French ⚖ 38 KB

The HPLC conditions associated with the retention times for the paclitaxel-related compounds listed in Table 1 should read as follows: RT=Retention times on an analytical HPLC (Waters) equipped with a reversed-phase column (Suplecosil C18) using gradient elution (60% acetonitrile in water going to 7