160582-75-2

Upstream product

• 150541-99-4 7,13-O,O-Bis(triethylsilyl)baccatin III 
• 160582-74-1 1-dimethylsilyl-7,13-bis(triethylsilane)baccatin III 

Downstream Products

• 160582-77-4 C₄₇H₇₄O₁₁Si₃ 
• 189006-03-9 10-deacetylbaccatin III 
• 160582-82-1 C₆₄H₈₁NO₁₄Si₂ 
• 160582-79-6 C₆₁H₈₁NO₁₄Si₂ 
• 160582-80-9 C₄₂H₅₄O₁₁Si 
• 160582-78-5 C₃₉H₅₄O₁₁Si 
• 1045727-73-8 C₃₆H₄₀O₁₁ 
• 1045726-80-4 C₃₃H₄₀O₁₁ 
• 165686-30-6 C₅₈H₇₈N₂O₁₅Si₂ 
• 165686-31-7 C₅₆H₈₂N₂O₁₆Si₂ 
• 165686-29-3 C₆₀H₈₀N₂O₁₄Si₂ 
• 165686-26-0 C₄₂H₅₃NO₁₄Si 
• 165686-27-1 C₃₈H₅₅NO₁₂Si 
• 165686-28-2 7-TES-4-aziridine baccatin 

Relevant academic research and scientific papers

Synthesis of 4-deacetyl-1-dimethylsilyl-7-triethylsilylbaccatin III

A one-pot trisilylation step to protect three hydroxyl groups of baccatin III (1), followed by hydride ester cleavage and base hydrolysis of a triethylsilyl ether at C13, provides efficient access to a key intermediate 9 (top path). This route removes two

The taxol pathway 10-O-acetyltransferase shows regioselective promiscuity with the oxetane hydroxyl of 4-deacetyltaxanes

The 10-deacetylbaccatin III:10β-O-acetyltransferase isolated from Taxus cuspidata regiospecifically transfers short-chain alkanoyl groups from their corresponding CoA thioesters to the C10 hydroxyl of 10-deacetylbaccatin III. This 10-O-acetyltransferase along with five other Taxus acyltransferases on the paclitaxel (Taxol) biosynthetic pathway and one additional Taxus-derived acyltransferases of unknown function were screened for 4-O-acetyltransferase activity against 4-deacetylbaccatin III, 7-acetyl-, 13-acetyl-, and 7,13-diacetyl-4-deacetylbaccatin III. These 4-deacyl derivatives were semisynthesized from the natural product baccatin III via silyl protecting group manipulation, regioselective reductive ester cleavage with sodium bis(2-methoxyethoxy)aluminum hydride, and regioselective acetylation with acetic anhydride. Assays with the 4-deacetylated diterpene substrates and acetyl CoA revealed the taxane 10β-O-acetyltransferase was able to catalyze the 4-O-acetylation of 4-deacetylbaccatin III to baccatin III and 13-acetyl-4-deacetylbacatin III to 13-acetylbaccatin III, although each was converted at lesser efficiency than with the natural substrate. In contrast, this enzyme was unable to acetylate 7-acetyl-4-deacetylbaccatin III and 7,13-diacetyl-4-deacetylbaccatin III substrates at C4, suggesting that the C7 hydroxyl of baccatin III must remain deacylated for enzyme function. The biocatalytic transfer of an acyl group to the tertiary hydroxyl on the oxetane moiety at C4 of the taxane ring demonstrates that the regiochemistry of the 10β-acetyltransferase is mutable.

First Syntheses of Novel Paclitaxel(Taxol) Analogs Modified at the C4-Position

A highly regiospecific method for the modification of paclitaxel at the C-4 position has been invented, as exemplified by the synthesis of the C-4 cyclopropyl ester of paclitaxel (4) and the C-4 benzoate of paclitaxel (5).