397250-01-0

Basic information

• Product Name: 14β-Hydroxy-13-oxo-7-O-(triethylsilyl) Baccatin III 1,14-Carbonate
• Synonyms: 14β-Hydroxy-13-oxo-7-O-(triethylsilyl) Baccatin III 1,14-Carbonate;IAVYJZKSOXQISM-VECNKZNOSA-N
• CAS NO: 397250-01-0
• Molecular Formula: C₃₈H₄₈O₁₃Si
• Molecular Weight: 740.86542
• Product Categories: Chiral Reagents, Heterocycles, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 397250-01-0.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• CAS DataBase Reference: 14β-Hydroxy-13-oxo-7-O-(triethylsilyl) Baccatin III 1,14-Carbonate(CAS DataBase Reference)
• NIST Chemistry Reference: 14β-Hydroxy-13-oxo-7-O-(triethylsilyl) Baccatin III 1,14-Carbonate(397250-01-0)
• EPA Substance Registry System: 14β-Hydroxy-13-oxo-7-O-(triethylsilyl) Baccatin III 1,14-Carbonate(397250-01-0)

Safety Data

• Hazardous Substances Data: 397250-01-0(Hazardous Substances Data)

Usage

Chemical Properties

14β-Hydroxy-13-oxo-7-O-(triethylsilyl) Baccatin III 1,14-Carbonate is White Foam

Uses

14β-Hydroxy-13-oxo-7-O-(triethylsilyl) Baccatin III 1,14-Carbonate is used in the preparation of Hydroxybaccatin III Carbonate derivatives.

Upstream product

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

Downstream Products

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

Relevant articles and documents

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.

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.