172018-16-5

Usage

Uses

13-epi-10-Deacetyl Baccatin III is a new analog of 10-Deacetylbaccatin III (D198250).

Upstream product

• 67-56-1 methanol 
• 71610-00-9 Cephalomannine 
• 71629-92-0 10-deacetyl-7-epi-baccatin III 
• 591-51-5 phenyllithium 
• 187961-12-2 C₂₈H₃₃Cl₃O₁₃ 
• 157664-03-4 7-β-D-xylosylbaccatin III 
• 90332-63-1 7-O-(β-xylosyl)-10-deacetyltaxol 
• 32981-86-5 10-deacetylbaccatin III 
• 151636-94-1 10-dehydro-10-deacetylbaccatin V 
• 191276-24-1 10-dehydro-10-deacetylbaccatin III (V) 
• 27548-93-2 baccatin III 
• 105454-04-4 7-epipaclitaxel 
• 148930-54-5 (2aR,4S,4aS,6R,9S,11S,12S,12bS)-6,12b-bis(acetyloxy)-9-({(2R,3S)-3-(benzoylamino)-3-phenyl-2-[(triethylsilyl)oxy]propanoyl}oxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9, 10,11,12,12a,12bdodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxet-12-yl benzoate 
• 187960-85-6 ((1S,5S,6R,7S,8S,9S,12S)-8,9-Dihydroxy-7,11,14,14-tetramethyl-3-oxo-12-triisopropylsilanyloxy-2,4-dioxa-tricyclo[8.3.1.0^1,5]tetradec-10-en-6-yl)-acetaldehyde 

Downstream Products

• 92950-41-9 7-acetyl-10-deacetyl baccatin III 
• 32981-90-1 7-O-acetylbaccatine III 
• 1431704-22-1 10-acetoxy-2-debenzoyl-2-(isoquinolin-7-yl)docetaxel 
• 1431704-23-2 10-acetoxy-2-debenzoyl-2-(quinolin-7-yl)docetaxel 
• 1431704-60-7 2'-O-(t-butyldimethylsilyl)-3'N-debenzoyl-3'N-Boc-3'C-dephenyl-3'C-(thiophen-3-yl)-7-O-(triethylsilyl)taxol 
• 1431704-62-9 2'-O-(t-butyldimethylsilyl)-3'N-debenzoyl-3'N-Boc-3'C-dephenyl-3'C-((benzo[d][1,3]dioxol-5-yl)-7-O-(triethylsilyl))taxol 
• 160747-92-2 3'N-debenzoyl-3'N-Boc-3'C-dephenyl-3'C-(thiophen-3-yl)taxol 
• 1431704-29-8 10-acetoxy-3'-debenzoyl-3'-[(3-hydroxymethyl)phenyl]docetaxel 
• 1431704-30-1 3'N-debenzoyl-3'N-Boc-3'C-dephenyl-3'C-((benzo[d][1,3]dioxol-5-yl))paclitaxel 
• 114915-16-1 10-deacetyl-7,10-diTroc-baccatin III 

Relevant academic research and scientific papers

Microbial transformation of 7-epi-10-deacetylbaccatin III to 10-deacetylbaccatin III

The microbial transformation of 7-epi-10-deacetylbaccatin III (7-epi-10-DAB III) to 10-deacetylbaccatin III (10-DAB III) was studied. In this report, seven microorganisms were found to be able to realize the transformation at yields from 20.0% to as high as 70.8%. The optimized conditions such as the solvent, pH value of the medium, the microorganisms, transformation time, and substrate concentration were investigated.

Reinvestigation to the C-7 epimerization of paclitaxel and related taxoids under basic conditions

Base-promoted C-7 epimerizations of paclitaxel, 10-deacetylbaccatin III were investigated. It has been found that 13α-OH may play an important role in the equilibrium of C-7 epimers of paclitaxel and related taxoids.

Microbial hydrolysis of 7-xylosyl-10-deacetyltaxol to 10-deacetyltaxol

Enterobacter sp. CGMCC 2487, a bacterial strain isolated from the soil around a Taxus cuspidata Sieb. et Zucc. plant, was able to remove the xylosyl group from 7-xylosyltaxanes. The xylosidase of this strain was an inducible enzyme. In the bioconversion of 7-xylosyl-10-deacetyltaxol (7-XDT) to 10-deacetyltaxol (10-DT), for the purpose of enhancing the conversion efficiency, the effects of NH4+, oat xylan, temperature, pH value, cell density and substrate concentration on the bioconversion have been systematically investigated. 3.0 mM NH4+, 0.6% oat xylan in the media could enhance the yield of 10-DT; the optimum biocatalytic temperature was 26 °C and optimum pH value was 6.0. The highest conversion rate and yield of 10-DT from 7-XDT reached 92% and 764 mg/L, respectively. In addition, the biocatalytic capacity of the cell cultures remained 66.1% after continuous three batches. These results indicate that converting 7-XDT to 10-DT, a useful intermediate for the semisynthesis of paclitaxel or other taxane-based anticancer drugs by a novel bacterial strain, Enterobacter sp. CGMCC 2487, would be an alternative for the practical application in the future.

Glycosyl hydrolase with beta-xylosidase and beta-glucosidase activities and uses thereof

A novel glycosyl hydrolase with activities of beta-xylosidase and beta-glucosidase is provided. Said glycosyl hydrolase can convert 7-xylosyltaxane compounds to 7-hydroxyltaxane compounds.

PROCESS FOR THE PURIFICATION 10-DEACETYBACCATINE III FROM 10-DEACETYL-2-DEBENZOYL-2-PENTENOYLBACCATINE III

A process for the preparation of 10-deacetyl-7,10-bis-trichloroacetylbaccatine III with HPLC purity higher than 99% and free from 2-debenzoyl-2-pentenoylbaccatine III by purification of 10-deacetyl-7,10-bis-trichloroacetylbaccatineIII followed by alkaline hydrolysis of the protecting groups in position 7 and 10.

Biological degradation of taxol by action of cultured cells on 7-acetyltaxol-2″-yl glucoside

Biodegradation pathways of taxol in cultured cells of Synechocystis sp. PCC 6803, Synechococcus sp. PCC 7942, Marchantia polymorpha, Nicotiana tabacum, and Glycine max were investigated using a water-soluble taxol derivative, 7-ace-tyltaxol-2″-yl glucoside, as the substrate. Although cyanobacteria, Synechocystis sp. PCC 6803 and Synechococcus sp. PCC 7942, and a lower plant, M. polymorpha, catalyzed the epimerization at 7-position of taxol skeleton, no epimerization occurred with higher plants, N. tabacum and G. max. On the other hand, Synechocystis sp. PCC 6803, Synechococcus sp. PCC 7942, M. polymorpha, and N. tabacum catalyzed hydrolysis at 13-position of taxol to give baccatin III and 10-deacetyl baccatin III. Both cyanobacteria cells also deacetylated 7-epi-baccatin III at its 10-position. M. polymorpha and G. max deacetylated at 10-position of taxol. Copyright

SEMI-SYNTHETIC ROUTE FOR THE PREPARATION OF PACLITAXEL, DOCETAXEL, AND 10-DEACETYLBACCATIN III FROM 9-DIHYDRO-13-ACETYLBACCATIN III

A novel semisynthetic route has been provided in the preparation of docetaxel and paclitaxel. This new process involves the conversion of 9-dihydro-13-acetylbaccatinIII to docetaxel and paclitaxel by the step of converting 9-dihydro-13-acetylbaccatin III into 7-O-triethylsilyl-9,10-diketobaccatin III, and adding docetaxel and paclitaxel side chain precursors, respectively, to form a new class of taxane intermediates, such as 7-O-triethylsilyl-9,10-diketodocetaxel and 7-O-triethylsilyl-9,10-diketopaclitaxeltaxel. These new intermediates then by a series reduction, acetylation of the 10-hydroxyl position for paclitaxel and finally deprotection to yield docetaxel and paclitaxel, the most important anti-cancer drugs.

CONVERSION 9-DIHYDRO-13-ACETYLBACCATIN III TO 10-DEACETYLBACCATIN III

The present invention relates to a process is provided for the conversion of 9-dihydro-13-acetylbaccatin to 10-deacetylbaccatin III. The process includes four specific interrelated steps. The first step involves protecting the 7-hydroxyl group of 9-dihydro-13-acetylbaccatin and converting that 7-hydroxyl-protected 9-dihydro-13-acetylbaccatin to 7, 13-diacetyl-9-dihydrobaccatin III. The second step involves reacting that 7, 13-diacetyl-9-dihydrobaccatin III with 4-methylmorpholine N-oxide in a suitable solvent and oxidizing that reaction product to yield 7, 13-diacetylbaccatin. The third step involves deacetylating that 7, 13-diacetyl-9-dihydrobaccatin III to yield 7-acetylbaccatin III. The fourth and final step involves converting that 7-acetylbaccatin III to 10-deacetylbaccatin III.

A PROCESS FOR THE PURIFICATION OF 10-DEACETYLBACCATINE III FROM 10-DE ACET YL-2- DEBENZOYL-2-PENTENOYLBACCATINE III

A process for the preparation of 10-deacetyl-7,10-bis- trichloroacetylbaccatine III with HPLC purity higher than 99% and free from 2-debenzoyl-2-pentenoylbaccatine III by purification of 10-deacetyl-7,10-bis- trichloroacetylbaccatineIII followed by alkaline hydrolysis of the protecting groups in position 7 and 10.

The Reductive Fragmentation of 7-Hydroxy-9,10-dioxotaxoids

The retro-aldol reductive fragmentation of different structural types of 7-hydroxy-9,10-dioxotaxoids was investigated, showing that the reaction is typical of taxanes and requires cerium(III) promotion with NaBH4 in protic medium and alkylboron (aluminium) hydrides in aprotic solvents. The resulting 7,8-seco-taxanes are key intermediates for the synthesis of a novel class of anticancer taxanes endowed with a unique pattern of in vivo biological activity. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.