397250-01-0

Usage

Uses

Used in Pharmaceutical Industry:
14β-Hydroxy-13-oxo-7-O-(triethylsilyl) Baccatin III 1,14-Carbonate is used as a key intermediate for the preparation of Hydroxybaccatin III Carbonate derivatives. These derivatives are crucial in the semi-synthesis of Taxol, a widely used anti-cancer drug that targets microtubules and inhibits cell division, leading to the prevention of tumor growth.
Chemical Properties:
14β-Hydroxy-13-oxo-7-O-(triethylsilyl) Baccatin III 1,14-Carbonate is a white foam, which indicates its physical state and appearance as a substance used in the pharmaceutical industry. This characteristic is important for its handling, storage, and use in chemical reactions and synthesis processes.

Upstream product

• 75-44-5 phosgene 
• 370110-84-2 13-dehydro-14β-hydroxy-7-triethylsilylbaccatin III 
• 530-62-1 1,1'-carbonyldiimidazole 
• 115437-21-3 7-(triethylsilyl)baccatin III 
• 150665-56-8 7-O-triethylsilyl-13-keto baccatin III 

Downstream Products

• 186347-84-2 14β-hydroxy-7-triethylsilylbaccatin III 1,14-carbonate 

Relevant academic research and scientific papers

The synthesis of novel taxoids for oral administration

A group of novel taxoids, with modifications at C-7, C-10, C-3′ and C-14 positions of paclitaxel, was synthesized in order to improve their biological profile by decreasing their affinity with P-glycoprotein (P-gp) and increasing cellular permeability. Most of the new taxoids demonstrated the similar potent cytotoxic activities in MCF-7 human tumor cell line as paclitaxel in vitro. In the permeability assay with monolayers of Caco-2 cells, most of the compounds demonstrated an increased trans-cellular transport in A-to-B direction in comparison with paclitaxel. Among them the compounds T-13, T-15 and T-26 showed the highest permeability, and with efflux ratios better than that of ortataxel. The interaction of the compounds T-13 and T-26 with P-gp was evaluated using Madin-Darby canine kidney (MDCK)-multidrug resistance-1(MDR1) and MDCK-wild-type (WT). The results indicated that T-13 and T-26 were poor substrates for P-gp and possessed inhibiting effects of P-gp mediated efflux. It was thus clear that simultaneous modifications at the C-7, C-10 and C-3′ positions of paclitaxel significantly impaired its interactions with P-gp and interfered with P-gp mediated efflux.

Process for the preparation of baccatin III derivatives

A process for the preparation of 14 beta-hydroxy-1,4-carbonate-deacetylbaccatin III and intermediates useful for the preparation of novel taxan derivatives with antitumor activity are disclosed.

Diastereoselective 14beta-hydroxylation of baccatin III derivatives.

14beta-Hydroxybaccatin III, a compound with limited availability by natural sources, is the starting material for the synthesis of the second-generation anticancer taxoid ortataxel. The 7-tert-butoxycarbonyl (1a) and 7-triethylsilyl (1b) derivatives of 14beta-hydroxybaccatin III 1,14-carbonate were synthesized from 10-deacetylbaccatin III (3). The crucial steps were (a) the C(14)beta hydroxylation of the corresponding 13-oxobaccatin III derivatives by oxaziridine-mediated electrophilic oxidation and (b) the reduction of the C(13) carbonyl group with sodium or alkylammonium borohydrides. This protocol provides a practical way for the semisynthesis of ortataxel from 10-deacetylbaccatin III, a compound readily available from various yews.