114915-16-1

Basic information

• Product Name: N-DES-T-BOC-10-DEACETYL-7,10-O-BIS{[(2,2,2-TRICHLOROETHYL)OXY]CARBONYL} DOCETAXEL
• Synonyms: N-DES-T-BOC-10-DEACETYL-7,10-O-BIS{[(2,2,2-TRICHLOROETHYL)OXY]CARBONYL} DOCETAXEL;(αR,βS)-β-AMino-α-hydroxy-benzenepropanoic Acid (2aR,4S,4aS,6R,9S,11S, 12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy
• CAS NO: 114915-16-1
• Molecular Formula: C₄₄H₄₇Cl₆NO₁₆
• Molecular Weight: 1058.55908
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites;Pharmaceuticals;Chiral Reagents;Inhibitors;Intermediates;Chiral Reagents, Inhibitors, Intermediates, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 114915-16-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• CAS DataBase Reference: N-DES-T-BOC-10-DEACETYL-7,10-O-BIS{[(2,2,2-TRICHLOROETHYL)OXY]CARBONYL} DOCETAXEL(CAS DataBase Reference)
• NIST Chemistry Reference: N-DES-T-BOC-10-DEACETYL-7,10-O-BIS{[(2,2,2-TRICHLOROETHYL)OXY]CARBONYL} DOCETAXEL(114915-16-1)
• EPA Substance Registry System: N-DES-T-BOC-10-DEACETYL-7,10-O-BIS{[(2,2,2-TRICHLOROETHYL)OXY]CARBONYL} DOCETAXEL(114915-16-1)

Safety Data

• Hazardous Substances Data: 114915-16-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Uses

Different sources of media describe the Uses of 114915-16-1 differently. You can refer to the following data:
1. A intermediate in the synthesis of a metabolite of Docetaxel, an antineoplastic.
2. An intermediate in partial synthesis of major human metabolites of Docetaxel (D494420), an antineoplastic.

Upstream product

• 114915-14-9 7,10-bis-O-(2,2,2-trichloroethoxycarbonyl)docetaxel 
• 143527-76-8 4-acetoxy-2α-benzoyloxy-5β,20-epoxy-1-hydroxy-9-oxo-7β,10β-bis[(2,2,2-tri-chloroethoxy)carbonyloxy]-11-taxen-13α-yl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate 
• 143615-00-3 (2R,3S)-3-amino-3-phenyl-2-hydroxypropionic acid ethyl ester 
• 144787-20-2 (2R,3S)-3-azido-2-hydroxy-benzenepropanoic acid ethyl ester 
• 100-52-7 benzaldehyde 
• 95603-44-4 7,10-di-(2,2,2-trichloroethyloxycarbonyl)-10-deacetylbaccatin III 
• 126060-73-9 ethyl (2R,3R)-3-phenyl-2,3-oxiranepropanoate 
• 114977-25-2 C₄₉H₅₅Cl₆NO₁₈ 
• 32981-86-5 10-deacetylbaccatin III 
• 144704-63-2 (4S,5R)-3-((2S,3R)-2-Bromo-3-hydroxy-3-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one 
• 143527-74-6 ethyl (4S,5R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-phenyl-5-oxazolidinecarboxylate 
• 143615-03-6 (4S,5R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-4-phenyloxazolidine-5-carboxylic acid 
• 143527-75-7 (2R,3S) ethyl N-(t-butoxycarbonyl)-3-phenylisoserine 

Downstream Products

• 78432-77-6 10-deacetylpaclitaxel 
• 114915-20-7 Docetaxel 
• 125354-12-3 C₅₁H₅₁Cl₆NO₁₇ 
• 114915-18-3 C₅₁H₅₁Cl₆NO₁₇ 
• 154044-74-3 N-de-t-butoxycarbonyl-N-2-<2-methyl-1-(4-methoxyphenyl)methoxy>propyloxycarbonyl-7,10-O-diTroc-docetaxel 

Relevant articles and documents

Design, synthesis and cytotoxicity of novel 3′-N-alkoxycarbonyl docetaxel analogs

By-product 9a exhibited potent cytotoxicity against both SK-OV-3 and A549 cell lines. The structure of 9a was characterized using 1D and 2D NMR experiments and confirmed by synthesis to afford a diastereomeric mixture (16a) that was identical to 9a, as well as a pair of diastereomers (R)-16b and (S)-16c. The preliminary SAR study demonstrated that analogs with an (R)-configuration were slightly more potent than analogs with an (S)-configuration. In addition, α,α-gem-dimethyl analogs 16g-i were the most potent analogs in this series, exhibiting similar potency to docetaxel and greater potency than Taxol against the SK-OV-3 cell line. For the A549 cell line, analogs 16g-i were more potent (>65-fold) than both docetaxel and Taxol.

Method for purifying docetaxel

The invention discloses a method for purifying docetaxel. A docetaxel solid precipitates from a dichloromethane and toluene mixed solution. The purifying method has the advantages of great reduction of the single content of every impurity in docetaxel, introduction of few impurities, improvement of the purity of the product, and high yield, and is very suitable for industrial large-scale production, and the obtained product meets preparation demands, and can be directly used to prepare a docetaxel injection.

Design, synthesis and biological evaluation of novel fluorinated docetaxel analogues

A series of novel fluorinated docetaxel analogues have been synthesized and evaluated in vitro and in vivo. Incorporated one, two or three fluorine atom(s) either at both meta position on C-2 benzolate and 3′-N-tert-butyloxyl group or only at 3′-N-tert-butyloxyl group has resulted in potent analogues which have comparable or superior in vitro and in vivo cytotoxicity to docetaxel. Among them, compounds 14d and 14e have displayed more potent cytotoxicity than docetaxel both in human cancer cell line SK-OV-3 in vitro and in human non-small cell lung cancer A549 xenografts in vivo. Preliminary data show that compound 14a has reduced acute animal toxicity in mice compared with docetaxel.