151636-94-1

Basic information

• Product Name: 10-Dehydrobaccatin V
• Synonyms: (2aR,4R,4aS,9S,11S,12S,12aR,12bS)-12b-(Acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,9,10,11,12,12a,12b-decahydro-4,9,11-trihydroxy-4a,8,13,13-tetraMethyl-7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete-5,6-dione;10-Deacetyl-10-oxo-baccatin V;10-Dehydrobaccatin V;7-epi-10-Oxo-10-deacetyl Baccatin III
• CAS NO: 151636-94-1
• Molecular Formula: C₂₉H₃₄O₁₀
• Molecular Weight: 542.57426
• Product Categories: Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 151636-94-1.mol

Chemical Properties

• Appearance: /
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• Stability: Hygroscopic
• CAS DataBase Reference: 10-Dehydrobaccatin V(CAS DataBase Reference)
• NIST Chemistry Reference: 10-Dehydrobaccatin V(151636-94-1)
• EPA Substance Registry System: 10-Dehydrobaccatin V(151636-94-1)

Safety Data

• Hazardous Substances Data: 151636-94-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
10-Dehydrobaccatin V is used as a precursor in the production of paclitaxel and its derivatives for [application reason] the development of anticancer drugs. Its role in the biosynthesis of paclitaxel makes it a valuable compound for the pharmaceutical industry, as it can potentially streamline the production process and increase the availability of this essential drug.
Used in Research and Development:
10-Dehydrobaccatin V is used as a research compound for [application reason] the study of its chemical properties, biosynthetic pathways, and potential applications in the development of new drugs and therapies. Its unique structure and role in the production of paclitaxel make it an interesting subject for scientific investigation.
Used in Quality Control:
10-Dehydrobaccatin V is used as a reference material for [application reason] quality control and assurance in the production of paclitaxel and its derivatives. As an impurity of paclitaxel, it is essential to monitor and control its presence in the final product to ensure the safety and efficacy of the drug.

Upstream product

• 32981-86-5 10-deacetylbaccatin III 

Downstream Products

• 172018-16-5 10-deacetyl Baccatin III 

Relevant articles and documents

Anomalous microbial transformations on the taxane ring of 10-DAB by a strain of the fungus Curvularia lunata: Transbenzoylation, transacetylation, and opening of the oxetane ring

The fermentation of 10-deacetylbaccatin III (10-DAB) (1) with Curvularia lunata afforded the taxane hemiacetals 2a and 3, characterized by extensive structural modification, including C-2 to C-1 transbenzoylation, oxidation of the C-2 hydroxyl, formation

PROCESSES FOR TAXANE DERIVATIVES AND INTERMEDIATES USEFUL THEREIN

The application provides a process for the preparation of taxane derivatives and intermediates useful in such processes.

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.

Synthesis of modified baccatins via an oxidation-reduction protocol

(12R)-7-trietylsilyl-11-dihydro-10-deacetylbaccatin III (2), -deacetylbaccatin III (4) and the 7,8-seco baccatin III (5a) were synthesized from 10-deacetylbaccatin III via an oxidation-reduction protocol.

THE CHEMISTRY AND OCCURRENCE OF TAXANE DERIVATIVES. XIII. THE OXIDATION OF 10-DEACETYLBACCATIN III

The three secondary hydroxyls of 10-deacetylbaccatin III, 1, can be selectively oxidized.However, only the 13-dehydro derivative is stable under the reaction conditions, whereas the 10- and the 7-dehydro derivatives undergo epimerization at C-7 and oxetan