76446-91-8

Basic information

• Product Name: 13-acetyl baccatin III
• Synonyms: 13-acetyl baccatin III
• CAS NO: 76446-91-8
• Molecular Weight: 628.673
• Mol File: 76446-91-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 13-acetyl baccatin III(CAS DataBase Reference)
• NIST Chemistry Reference: 13-acetyl baccatin III(76446-91-8)
• EPA Substance Registry System: 13-acetyl baccatin III(76446-91-8)

Safety Data

• Hazardous Substances Data: 76446-91-8(Hazardous Substances Data)

Upstream product

• 1089203-99-5 13-acetyl-4-deacetylbaccatin III 
• 72-89-9 acetylcoenzyme A 
• 71610-00-9 Cephalomannine 
• 290815-46-2 7-triisopropylsilyl-13-acetylbaccatin III 
• 142203-65-4 13-acetyl-9-dihydrobaccatin III 
• 115437-18-8 7-triethylsilyl-10-deacetylbaccatin III 
• 290815-48-4 7-epi-13-acetylbaccatin III 
• 152448-78-7 13-Acetyl-7-(triethylsilyl)baccatin III 
• 103150-34-1 13-acetyl-7-(2,2,2-trichloroethyloxycarbonyl)baccatin III 
• 108-24-7 acetic anhydride 
• 27548-93-2 baccatin III 

Downstream Products

• 848250-67-9 C₄₂H₄₆O₁₄ 
• 848251-54-7 C₄₈H₆₀O₁₄Si 

Relevant articles and documents

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.

Taxus canadensis abundant taxane: Conversion to paclitaxel and rearrangements

An efficient conversion of Taxus canadensis abundant taxane, 9-dihydro-13-acetylbaccatin III to baccatin III is described. Since the synthesis of paclitaxel from baccatin III has been reported, this work can be used for additional supply of this powerful anticancer drug. In addition, new taxanes derived from skeletal rearrangements originating from oxidation-reduction reactions of the Canadian yew major taxane, are reported. Copyright (C) 2000 Elsevier Science Ltd.

Modified Taxols. 3. Preparation and Acylation of Baccatin III

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