162081-12-1

Basic information

• Product Name: 7-O-(2-chloroacetyl)paclitaxel
• Synonyms: 7-O-(2-chloroacetyl)paclitaxel
• CAS NO: 162081-12-1
• Molecular Weight: 930.403
• Mol File: 162081-12-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 7-O-(2-chloroacetyl)paclitaxel(CAS DataBase Reference)
• NIST Chemistry Reference: 7-O-(2-chloroacetyl)paclitaxel(162081-12-1)
• EPA Substance Registry System: 7-O-(2-chloroacetyl)paclitaxel(162081-12-1)

Safety Data

• Hazardous Substances Data: 162081-12-1(Hazardous Substances Data)

Upstream product

• 632335-28-5 7-O-[2-(chloroacetyl)]-13-[(4S,5R)-2-p-methoxyphenyl-4-phenyl-3-[(2-trimethylsilyl)ethoxy-carbonyl]-1,3-oxazolidinyl-5-carbonyl] baccatin III 
• 98-88-4 benzoyl chloride 
• 632335-29-6 7-chloroacetyl-13-[(4S,5R)-2,2'-dimethyl-4-phenyl-3-[(2-trimethylsilyl)ethoxycarbonyl]-1,3-oxazolidinyl-5-carbonyl] baccatin III 
• 632335-26-3 7-O-[2-(chloroacetyl)]-13-[(4S,5R)-2-p-methoxyphenyl-4-phenyl-3-[(2-phenyl-2-trimethylsilyl)ethoxycarbonyl]-1,3-oxazolidinyl-5-carbonyl] baccatin III 
• 33069-62-4 taxol 
• 114655-02-6 2'-O-(tert-butyldimethylsilyl)paclitaxel 
• 611226-72-3 C₅₅H₆₆ClNO₁₅Si 

Downstream Products

• 33069-62-4 taxol 

Relevant articles and documents

Method of preparation of anticancer taxanes using 3-[(substituted-2-trialkylsilyl)ethoxycarbonyl]-5-oxazolidine carboxylic acids

This invention relates to a process for preparation of taxanes comprising subjecting 7,10-diprotected intermediates 7-O-(2-haloacyl) baccatin III 6c or 7,10-O-di-(2-haloacyl)-10-deacetylbaccatin III 6b to a step of coupling with (4S,5R)-3-[(2-alkyl/aryl-2-trialkylsilyl) ethoxy-carbonyl]-4-aryl-2-substituted-1,3-oxazolidine-5-carboxylic acid 1 in the presence of a condensation agent, an activating agent and an aromatic hydrocarbon to obtain 7-O-[2-(haloacyl)]-13-[(4S,5R)-4-aryl-2-substituted-3(2-unsubstituted/substituted-2-trialkylsilyl)-ethoxycarbonyl-1,3-oxazolidinyl-5-carbonyl]baccatin III 7a or 7,10-di-O[2-(haloacyl)]-13-[(4S,5R)-4-aryl-2-substituted-3-(2-unsubstituted/substituted-2-trialkylsilyl)ethoxy-carbonyl-1,3-oxazolidinyl-5-carbonyl]-10-deacetylbaccatin III 7b; treating the coupled products 7-O-[2-(haloacyl)]-13-[(4S,5R)-4-aryl-2-substituted-3-(2-substituted-2-trialkylsilyl)ethoxy-carbonyl-1,3-oxazolidinyl-S-carbonyl]baccatin III 7a or 7,10-di-0-[2[(haloacyl)]-13-[(4S,5R)-4-aryl-2-substituted-3-(2-substituted-2-trialkylsilyl)ethoxycarbonyl-1,3-oxazolidinyl-5-carbonyl]-10-deacetylbaccatin III 7b with tetraalkylammonium halide in a haloalkane to obtain free amine of structure 8; treating free amine 8 with acid chloride or acid anhydride in the presence of a base in a heterogeneous phase to obtain the intermediates of structure 9; subjecting the intermediates of compound 9 to the deprotection of 2-haloacyl group under mild alkaline condition at ?20 to +40° C. for 6-24 h in the presence of ammonia or aliphatic amines or aromatic amines or their combination to obtain paclitaxel or docetaxel.

Mechanistic considerations pertaining to the solvolysis of paclitaxel analogs bearing ester groups at the C2′ position

Dilute solutions of paclitaxel-related derivatives having chloroacetyl esters in the C2′ position undergo ready methanolysis according to pseudo first-order kinetics while more concentrated solutions appear to be stabilized, possibly by the formation of h